Search for "photoactivation" in Full Text gives 21 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98
Graphical Abstract
Scheme 1: DTBP-mediated oxidative alkylarylation of activated alkenes.
Scheme 2: Iron-catalyzed oxidative 1,2-alkylarylation.
Scheme 3: Possible mechanism for the iron-catalyzed oxidative 1,2-alkylation of activated alkenes.
Scheme 4: A metal-free strategy for synthesizing 3,3-disubstituted oxindoles.
Scheme 5: Iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkenes.
Scheme 6: Proposed mechanism for the iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkene...
Scheme 7: Bicyclization of 1,n-enynes with alkyl nitriles.
Scheme 8: Possible reaction mechanism for the bicyclization of 1,n-enynes with alkyl nitriles.
Scheme 9: Radical cyclization of N-arylacrylamides with isocyanides.
Scheme 10: Plausible mechanism for the radical cyclization of N-arylacrylamides with isocyanides.
Scheme 11: Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds.
Scheme 12: Plausible mechanism for the dehydrogenative cyclization of 1,3-dicarbonyl compounds.
Scheme 13: Photocatalyzed cyclization of N-arylacrylamide and N,N-dimethylaniline.
Scheme 14: Proposed mechanism for the photocatalyzed cyclization of N-arylacrylamides and N,N-dimethylanilines....
Scheme 15: Electrochemical monofluoroalkylation cyclization of N-arylacrylamides with dimethyl 2-fluoromalonat...
Scheme 16: Proposed mechanism for the electrochemical radical cyclization of N-arylacrylamides with dimethyl 2...
Scheme 17: Photoelectrocatalytic carbocyclization of unactivated alkenes using simple malonates.
Scheme 18: Plausible mechanism for the photoelectrocatalytic carbocyclization of unactivated alkenes with simp...
Scheme 19: Bromide-catalyzed electrochemical trifluoromethylation/cyclization of N-arylacrylamides.
Scheme 20: Proposed mechanism for the electrochemical trifluoromethylation/cyclization of N-arylacrylamides.
Scheme 21: Visible light-mediated trifluoromethylarylation of N-arylacrylamides.
Scheme 22: Plausible reaction mechanism for the visible light-mediated trifluoromethylarylation of N-arylacryl...
Scheme 23: Electrochemical difluoroethylation cyclization of N-arylacrylamides with sodium difluoroethylsulfin...
Scheme 24: Electrochemical difluoroethylation cyclization of N-methyacryloyl-N-alkylbenzamides with sodium dif...
Scheme 25: Photoredox-catalyzed radical aryldifluoromethylation of N-arylacrylamides with S-(difluoromethyl)su...
Scheme 26: Proposed mechanism for the photoredox-catalyzed radical aryldifluoromethylation of N-arylacrylamide...
Scheme 27: Visible-light-induced domino difluoroalkylation/cyclization of N-cyanamide alkenes.
Scheme 28: Proposed mechanism of photoredox-catalyzed radical domino difluoroalkylation/cyclization of N-cyana...
Scheme 29: Palladium-catalyzed oxidative difunctionalization of alkenes.
Scheme 30: Two possible mechanisms of palladium-catalyzed oxidative difunctionalization.
Scheme 31: Silver-catalyzed oxidative 1,2-alkyletherification of unactivated alkenes with α-bromoalkylcarbonyl...
Scheme 32: Photochemical radical cascade cyclization of dienes.
Scheme 33: Proposed mechanism for the photochemical radical cascade 6-endo cyclization of dienes with α-carbon...
Scheme 34: Photocatalyzed radical coupling/cyclization of N-arylacrylamides and.
Scheme 35: Photocatalyzed radical-type couplings/cyclization of N-arylacrylamides with sulfoxonium ylides.
Scheme 36: Possible mechanism of visible-light-induced radical-type couplings/cyclization of N-arylacrylamides...
Scheme 37: Visible-light-promoted difluoroalkylated oxindoles systhesis via EDA complexes.
Scheme 38: Possible mechanism for the visible-light-promoted radical cyclization of N-arylacrylamides with bro...
Scheme 39: A dicumyl peroxide-initiated radical cascade reaction of N-arylacrylamide with DCM.
Scheme 40: Possible mechanism of radical cyclization of N-arylacrylamides with DCM.
Scheme 41: An AIBN-mediated radical cascade reaction of N-arylacrylamides with perfluoroalkyl iodides.
Scheme 42: Possible mechanism for the reaction with perfluoroalkyl iodides.
Scheme 43: Photoinduced palladium-catalyzed radical annulation of N-arylacrylamides with alkyl halides.
Scheme 44: Radical alkylation/cyclization of N-Alkyl-N-methacryloylbenzamides with alkyl halides.
Scheme 45: Possible mechanism for the alkylation/cyclization with unactivated alkyl chlorides.
Scheme 46: Visible-light-driven palladium-catalyzed radical cascade cyclization of N-arylacrylamides with unac...
Scheme 47: NHC-catalyzed radical cascade cyclization of N-arylacrylamides with alkyl bromides.
Scheme 48: Possible mechanism of NHC-catalyzed radical cascade cyclization.
Scheme 49: Electrochemically mediated radical cyclization reaction of N-arylacrylamides with freon-type methan...
Scheme 50: Proposed mechanistic pathway of electrochemically induced radical cyclization reaction.
Scheme 51: Redox-neutral photoinduced radical cascade cylization of N-arylacrylamides with unactivated alkyl c...
Scheme 52: Proposed mechanistic hypothesis of redox-neutral radical cascade cyclization.
Scheme 53: Thiol-mediated photochemical radical cascade cylization of N-arylacrylamides with aryl halides.
Scheme 54: Proposed possible mechanism of thiol-mediated photochemical radical cascade cyclization.
Scheme 55: Visible-light-induced radical cascade bromocyclization of N-arylacrylamides with NBS.
Scheme 56: Possible mechanism of visible-light-induced radical cascade cyclization.
Scheme 57: Decarboxylation/radical C–H functionalization by visible-light photoredox catalysis.
Scheme 58: Plausible mechanism of visible-light photoredox-catalyzed radical cascade cyclization.
Scheme 59: Visible-light-promoted tandem radical cyclization of N-arylacrylamides with N-(acyloxy)phthalimides....
Scheme 60: Plausible mechanism for the tandem radical cyclization reaction.
Scheme 61: Visible-light-induced aerobic radical cascade alkylation/cyclization of N-arylacrylamides with alde...
Scheme 62: Plausible mechanism for the aerobic radical alkylarylation of electron-deficient amides.
Scheme 63: Oxidative decarbonylative [3 + 2]/[5 + 2] annulation of N-arylacrylamide with vinyl acids.
Scheme 64: Plausible mechanism for the decarboxylative (3 + 2)/(5 + 2) annulation between N-arylacrylamides an...
Scheme 65: Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2.
Scheme 66: Plausible mechanism for the rhenium-catalyzed decarboxylative annulation of N-arylacrylamides with ...
Scheme 67: Visible-light-induced one-pot tandem reaction of N-arylacrylamides.
Scheme 68: Plausible mechanism for the visible-light-initiated tandem synthesis of difluoromethylated oxindole...
Scheme 69: Copper-catalyzed redox-neutral cyanoalkylarylation of activated alkenes with cyclobutanone oxime es...
Scheme 70: Plausible mechanism for the copper-catalyzed cyanoalkylarylation of activated alkenes.
Scheme 71: Photoinduced alkyl/aryl radical cascade for the synthesis of quaternary CF3-attached oxindoles.
Scheme 72: Plausible photoinduced electron-transfer (PET) mechanism.
Scheme 73: Photoinduced cerium-mediated decarboxylative alkylation cascade cyclization.
Scheme 74: Plausible reaction mechanism for the decarboxylative radical-cascade alkylation/cyclization.
Scheme 75: Metal-free oxidative tandem coupling of activated alkenes.
Scheme 76: Control experiments and possible mechanism for 1,2-carbonylarylation of alkenes with carbonyl C(sp2...
Scheme 77: Silver-catalyzed acyl-arylation of activated alkenes with α-oxocarboxylic acids.
Scheme 78: Proposed mechanism for the decarboxylative acylarylation of acrylamides.
Scheme 79: Visible-light-mediated tandem acylarylation of olefines with carboxylic acids.
Scheme 80: Proposed mechanism for the radical cascade cyclization with acyl radical via visible-light photored...
Scheme 81: Erythrosine B-catalyzed visible-light photoredox arylation-cyclization of N-arylacrylamides with ar...
Scheme 82: Electrochemical cobalt-catalyzed radical cyclization of N-arylacrylamides with arylhydrazines or po...
Scheme 83: Proposed mechanism of radical cascade cyclization via electrochemical cobalt catalysis.
Scheme 84: Copper-catalyzed oxidative tandem carbamoylation/cyclization of N-arylacrylamides with hydrazinecar...
Scheme 85: Proposed reaction mechanism for the radical cascade cyclization by copper catalysis.
Scheme 86: Visible-light-driven radical cascade cyclization reaction of N-arylacrylamides with α-keto acids.
Scheme 87: Proposed mechanism of visible-light-driven cascade cyclization reaction.
Scheme 88: Peroxide-induced radical carbonylation of N-(2-methylallyl)benzamides with methyl formate.
Scheme 89: Proposed cyclization mechanism of peroxide-induced radical carbonylation with N-(2-methylallyl)benz...
Scheme 90: Persulfate promoted carbamoylation of N-arylacrylamides and N-arylcinnamamides.
Scheme 91: Proposed mechanism for the persulfate promoted radical cascade cyclization reaction of N-arylacryla...
Scheme 92: Photocatalyzed carboacylation with N-arylpropiolamides/N-alkyl acrylamides.
Scheme 93: Plausible mechanism for the photoinduced carboacylation of N-arylpropiolamides/N-alkyl acrylamides.
Scheme 94: Electrochemical Fe-catalyzed radical cyclization with N-arylacrylamides.
Scheme 95: Plausible mechanism for the electrochemical Fe-catalysed radical cyclization of N-phenylacrylamide.
Scheme 96: Substrate scope of the selective functionalization of various α-ketoalkylsilyl peroxides with metha...
Scheme 97: Proposed reaction mechanism for the Fe-catalyzed reaction of alkylsilyl peroxides with methacrylami...
Scheme 98: EDA-complex mediated C(sp2)–C(sp3) cross-coupling of TTs and N-methyl-N-phenylmethacrylamides.
Scheme 99: Proposed mechanism for the synthesis of oxindoles via EDA complex.
Beilstein J. Org. Chem. 2025, 21, 854–863, doi:10.3762/bjoc.21.69
Graphical Abstract
Figure 1: A) Energy transfer catalysis of alkenes in organic synthesis. B) Energy transfer catalysis of conju...
Figure 2: Probing boron effects on reactivity (A) and confirming the generation of a photostationary state eq...
Figure 3: Probing EnT catalysis enabled [2 + 2] cycloaddition of simple alkenylboronic esters.
Scheme 1: Establishing the substrate scope. Conditions: 3 (1 equiv), xanthone (20 mol %), MeCN (0.03 M), unde...
Scheme 2: A) Product derivatization and B) transition-metal EnT catalysis. Reaction conditions A): 4d (1 equi...
Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56
Graphical Abstract
Figure 1: Structure-guided approach for engineering the (non-covalent) fluorescent light-up aptamer Pepper in...
Scheme 1: Chemical structures of the HBC dye family [7]. Variations to HBC530 highlighted in red color. All dyes...
Scheme 2: Synthesis of bromoalkyl HBC derivatives 7, 8, and 9.
Scheme 3: Synthesis of the HBC ether derivative 11.
Figure 2: Pepper aptamer reacts with different HBC derivatives. Chemical structures of the HBC derivatives us...
Scheme 4: Derivatization of the HBC fluorophore 5 to generate handles with distinct electrophilic groups.
Scheme 5: Synthesis of mesylated HBC fluorophores 16, 17, and 18.
Scheme 6: Synthesis of the bifunctional HBC fluorophore 22. For an application of 22 (pulldown of circular Pe...
Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30
Graphical Abstract
Scheme 1: “Precursor approach” for the synthesis of π-conjugated polycyclic compounds, with the thermally- or...
Scheme 2: Valence isomerization of chalcogen heteropines and subsequent cheletropic extrusion in the case of ...
Scheme 3: Early example of phenanthrene synthesis via a chemically-induced S-extrusion (and concomitant decar...
Scheme 4: Top: Conversion of dinaphthothiepine bisimides 3a,b and their sulfoxide analogues 4a,b into PBIs 6a,...
Figure 1: Top view (a) and side view (b) of the X-ray crystal structure of thiepine 3b showing its bent confo...
Scheme 5: Modular synthetic route towards dinaphthothiepines 3a–f and the corresponding S-oxides 4a–d, incorp...
Scheme 6: Top: Conversion of dithienobenzothiepine monomeric units into dithienonaphthalenes, upon S-extrusio...
Scheme 7: Synthesis of S-doped extended triphenylene derivative 22 from 3-bromothiophene (17) with the therma...
Scheme 8: Top: Synthesis of thermally-stable O-doped HBC 26a. Bottom: Synthesis of S- and Se-based soluble pr...
Scheme 9: Synthesis of dinaphthooxepine bisimide 33 and conversion into PBI 6f by O-extrusion triggered by el...
Figure 2: Cyclic voltammogram of dinaphthooxepine 33, evidencing the irreversibility of the reduction process...
Scheme 10: Top: Early example of 6-membered ring contraction with concomitant S-extrusion leading to dinaphtho...
Scheme 11: Examples of S-extrusion from annelated 1,2-dithiins under photoactivation (top) or thermal activati...
Scheme 12: Synthesis of dibenzo[1,4]dithiapentalene upon photoextrusion of SO2 [78].
Scheme 13: Extrusion of SO in naphthotrithiin-2-oxides for the synthesis of 2,5-dihydrothiophene 1-oxides [79].
Scheme 14: SO-extrusion as a key step in the synthesis of fullerenes (C60 and C70) encapsulating H2 molecules [80,82]....
Scheme 15: Synthesis of diepoxytetracene precursor 56 and its on-surface conversion into tetracene upon O-extr...
Scheme 16: Soluble precursors of hexacene, decacene and dodecacene incorporating 1,4-epoxides in their hydroca...
Scheme 17: Synthesis of tetraepoxide 59 as soluble precursor of decacene [85].
Figure 3: Constant-height STM measurement of decacene on Au(111) using a CO-functionalized tip (sample voltag...
Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131
Graphical Abstract
Scheme 1: Photocatalytic decarboxylative transformations mediated by the NaI/PPh3 catalyst system.
Scheme 2: Proposed catalytic cycle of NaI/PPh3 photoredox catalysis.
Scheme 3: Decarboxylative alkenylation of redox-active esters by NaI/PPh3 catalysis.
Scheme 4: Decarboxylative alkenylation mediated by NaI/PPh3 catalysis.
Scheme 5: NaI-mediated photoinduced α-alkenylation of Katritzky salts 7.
Scheme 6: n-Bu4NI-mediated photoinduced decarboxylative olefination.
Scheme 7: Proposed mechanism of the n-Bu4NI-mediated photoinduced decarboxylative olefination.
Scheme 8: Photodecarboxylative alkylation of redox-active esters with diazirines.
Scheme 9: Photoinduced iodine-anion-catalyzed decarboxylative/deaminative C–H alkylation of enamides.
Scheme 10: Photocatalytic C–H alkylation of coumarins mediated by NaI/PPh3 catalysis.
Scheme 11: Photoredox alkylation of aldimines by NaI/PPh3 catalysis.
Scheme 12: Photoredox C–H alkylation employing ammonium iodide.
Scheme 13: NaI/PPh3/CuBr cooperative catalysis for photocatalytic C(sp3)–O/N cross-coupling reactions.
Scheme 14: Proposed mechanism of NaI/PPh3/CuBr cooperative catalysis for photocatalytic C(sp3)–O/N cross-coupl...
Scheme 15: Photocatalytic decarboxylative [3 + 2]/[4 + 2] annulation between enynals and γ,σ-unsaturated N-(ac...
Scheme 16: Proposed mechanism for the decarboxylative [3 + 2]/[4 + 2] annulation.
Scheme 17: Decarboxylative cascade annulation of alkenes/1,6-enynes with N-hydroxyphthalimide esters.
Scheme 18: Decarboxylative radical cascade cyclization of N-arylacrylamides.
Scheme 19: NaI/PPh3-driven photocatalytic decarboxylative radical cascade alkylarylation.
Scheme 20: Proposed mechanism of the NaI/PPh3-driven photocatalytic decarboxylative radical cascade cyclizatio...
Scheme 21: Visible-light-promoted decarboxylative cyclization of vinylcycloalkanes.
Scheme 22: NaI/PPh3-mediated photochemical reduction and amination of nitroarenes.
Scheme 23: PPh3-catalyzed alkylative iododecarboxylation with LiI.
Scheme 24: Visible-light-triggered iodination facilitated by N-heterocyclic carbenes.
Scheme 25: Visible-light-induced photolysis of phosphonium iodide salts for monofluoromethylation.
Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23
Graphical Abstract
Figure 1: Examples of terpenes containing a bicyclo[3.6.0]undecane motif.
Figure 2: Commercially available first and second generation Grubbs and Hoveyda–Grubbs catalysts.
Figure 3: Examples of strategies to access the fusicoccan and ophiobolin tricyclic core structure by RCM.
Scheme 1: Synthesis of bicyclic core structure 12 of ophiobolin M (13) and cycloaraneosene (14).
Scheme 2: Synthesis of the core structure 21 of ophiobolins and fusicoccanes.
Scheme 3: Ring-closing metathesis attempts starting from thioester 22.
Scheme 4: Total synthesis of ent-fusicoauritone (28).
Figure 4: General structure of ophiobolins and congeners.
Scheme 5: Total synthesis of (+)-ophiobolin A (8).
Scheme 6: Investigation of RCM for the synthesis of ophiobolin A (8). Path A) RCM with TBDPS-protected alcoho...
Scheme 7: Synthesis of the core structure of cotylenin A aglycon, cotylenol (50).
Scheme 8: Synthesis of tricyclic core structure of fusicoccans.
Scheme 9: Total synthesis of (−)-teubrevin G (59).
Scheme 10: Synthesis of the core skeleton 63 of the basmane family.
Scheme 11: Total synthesis of (±)-schindilactone A (68).
Scheme 12: Total synthesis of dactylol (72).
Scheme 13: Ring-closing metathesis for the total synthesis of (±)-asteriscanolide (2).
Scheme 14: Synthesis of the simplified skeleton of pleuromutilin (1).
Scheme 15: Total synthesis of (−)-nitidasin (93) using a ring-closing metathesis to construct the eight-member...
Scheme 16: Total synthesis of (±)-naupliolide (97).
Scheme 17: Synthesis of the A-B ring structure of fusicoccane (101).
Scheme 18: First attempts of TRCM of dienyne substrates.
Scheme 19: TRCM on optimized substrates towards the synthesis of ophiobolin A (8).
Scheme 20: Tandem ring-closing metathesis for the synthesis of variecolin intermediates 114 and 115.
Scheme 21: Synthesis of poitediol (118) using the allylsilane ring-closing metathesis.
Scheme 22: Access to scaffold 122 by a NHK coupling reaction.
Scheme 23: Key step to construct the [5-8] bicyclooctanone core of aquatolide (4).
Scheme 24: Initial strategy to access aquatolide (4).
Scheme 25: Synthetic plan to cotylenin A (130).
Scheme 26: [5-8] Bicyclic structure of brachialactone (7) constructed by a Mizoroki–Heck reaction.
Scheme 27: Influence of the replacement of the allylic alcohol moiety.
Scheme 28: Formation of variecolin intermediate 140 through a SmI2-mediated Barbier-type reaction.
Scheme 29: SmI2-mediated ketyl addition. Pleuromutilin (1) eight-membered ring closure via C5–C14 bond formati...
Scheme 30: SmI2-mediated dialdehyde cyclization cascade of [5-8-6] pleuromutilin scaffold 149.
Scheme 31: A) Modular synthetic route to mutilin and pleuromutilin family members by Herzon’s group. B) Scaffo...
Scheme 32: Photocatalyzed oxidative ring expansion in pleuromutilin (1) total synthesis.
Scheme 33: Reductive radical cascade cyclization route towards (−)-6-epi-ophiobolin N (168).
Scheme 34: Reductive radical cascade cyclization route towards (+)-6-epi-ophiobolin A (173).
Scheme 35: Radical 8-endo-trig-cyclization of a xanthate precursor.
Figure 5: Structural representations of hypoestin A (177), albolic acid (178), and ceroplastol II (179) beari...
Scheme 36: Synthesis of the common [5-8-5] tricyclic intermediate of hypoestin A (177), albolic acid (178), an...
Scheme 37: Asymmetric synthesis of hypoestin A (177), albolic acid (178), and ceroplastol II (179).
Figure 6: Scope of the Pauson–Khand reaction.
Scheme 38: Nazarov cyclization revealing the fusicoauritone core structure 192.
Scheme 39: Synthesis of fusicoauritone (28) through Nazarov cyclization.
Scheme 40: (+)-Epoxydictymene (5) synthesis through a Nicholas cyclization followed by a Pauson–Khand reaction...
Scheme 41: Synthesis of aquatolide (4) by a Mukaiyama-type aldolisation.
Scheme 42: Tandem Wolff/Cope rearrangement furnishing the A-B bicyclic moiety 204 of variecolin.
Scheme 43: Asymmetric synthesis of the A-B bicyclic core 205 and 206 of variecolin.
Scheme 44: Formation of [5-8]-fused rings by cyclization under thermal activation.
Scheme 45: Construction of the [5-8-6] tricyclic core structure of variecolin (3) by Diels–Alder reaction.
Scheme 46: Synthesis of the [6-4-8-5]-tetracyclic skeleton by palladium-mediated cyclization.
Scheme 47: Access to the [5-8] bicyclic core structure of asteriscanolide (227) through rhodium-catalyzed cycl...
Scheme 48: Total syntheses of asterisca-3(15),6-diene (230) and asteriscanolide (2) with a Rh-catalyzed cycliz...
Scheme 49: Photocyclization of 2-pyridones to access the [5-8-5] backbone of fusicoccanes.
Scheme 50: Total synthesis of (+)-asteriscunolide D (245) and (+)-aquatolide (4) through photocyclization.
Scheme 51: Biocatalysis pathway to construct the [5-8-5] tricyclic scaffold of brassicicenes.
Scheme 52: Influence of the CotB2 mutant over the cyclization’s outcome of GGDP.
Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202
Graphical Abstract
Figure 1: Uncaging of peptide backbone N–H bonds from Chan–Lam-type modification.
Figure 2: Photocleavage of compounds 1 and 6 under basic conditions. Yield of products was calculated from cr...
Figure 3: (a) Photocleavage of compound 6 under acidic conditions. Yields determined by 1H NMR using residual...
Figure 4: Preparation and hydrolysis kinetics (inset) of N-formyl product 11. Dashed line: first-order decay ...
Figure 5: Proposed mechanism for the formation of aldehyde 3 and N-formyl product 8.
Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147
Graphical Abstract
Figure 1: Concept of dual synergistic catalysis.
Figure 2: Classification of catalytic systems involving two catalysts.
Figure 3: General mechanism for the dual nickel/photoredox catalytic system.
Figure 4: General mechanisms for C–H activation catalysis involving different reoxidation strategies.
Figure 5: Indole synthesis via dual C–H activation/photoredox catalysis.
Figure 6: Proposed mechanism for the indole synthesis via dual catalysis.
Figure 7: Oxidative Heck reaction on arenes via the dual catalysis.
Figure 8: Proposed mechanism for the Heck reaction on arenes via dual catalysis.
Figure 9: Oxidative Heck reaction on phenols via the dual catalysis.
Figure 10: Proposed mechanism for the Heck reaction on phenols via dual catalysis.
Figure 11: Carbazole synthesis via dual C–H activation/photoredox catalysis.
Figure 12: Proposed mechanism for the carbazole synthesis via dual catalysis.
Figure 13: Carbonylation of enamides via the dual C–H activation/photoredox catalysis.
Figure 14: Proposed mechanism for carbonylation of enamides via dual catalysis.
Figure 15: Annulation of benzamides via the dual C–H activation/photoredox catalysis.
Figure 16: Proposed mechanism for the annulation of benzamides via dual catalysis.
Figure 17: Synthesis of indoles via the dual C–H activation/photoredox catalysis.
Figure 18: Proposed mechanism for the indole synthesis via dual catalysis.
Figure 19: General concept of dual catalysis merging C–H activation and photoredox catalysis.
Figure 20: The first example of dual catalysis merging C–H activation and photoredox catalysis.
Figure 21: Proposed mechanism for the C–H arylation with diazonium salts via dual catalysis.
Figure 22: Dual catalysis merging C–H activation/photoredox using diaryliodonium salts.
Figure 23: Direct arylation via the dual catalytic system reported by Xu.
Figure 24: Direct arylation via dual catalytic system reported by Balaraman.
Figure 25: Direct arylation via dual catalytic system reported by Guo.
Figure 26: C(sp3)–H bond arylation via the dual Pd/photoredox catalytic system.
Figure 27: Acetanilide derivatives acylation via the dual C–H activation/photoredox catalysis.
Figure 28: Proposed mechanism for the C–H acylation with α-ketoacids via dual catalysis.
Figure 29: Acylation of azobenzenes via the dual catalysis C–H activation/photoredox.
Figure 30: C2-acylation of indoles via the dual C–H activation/photoredox catalysis.
Figure 31: Proposed mechanism for the C2-acylation of indoles with aldehydes via dual catalysis.
Figure 32: C2-acylation of indoles via the dual C–H activation/photoredox catalysis.
Figure 33: Perfluoroalkylation of arenes via the dual C–H activation/photoredox catalysis.
Figure 34: Proposed mechanism for perfluoroalkylation of arenes via dual catalysis.
Figure 35: Sulfonylation of 1-naphthylamides via the dual C–H activation/photoredox catalysis.
Figure 36: Proposed mechanism for sulfonylation of 1-naphthylamides via dual catalysis.
Figure 37: meta-C–H Alkylation of arenes via visible-light metallaphotocatalysis.
Figure 38: Alternative procedure for meta-C–H alkylation of arenes via metallaphotocatalysis.
Figure 39: Proposed mechanism for meta-C–H alkylation of arenes via metallaphotocatalysis.
Figure 40: C–H borylation of arenes via visible-light metallaphotocatalysis.
Figure 41: Proposed mechanism for C–H borylation of arenes via visible-light metallaphotocatalysis.
Figure 42: Undirected C–H aryl–aryl cross coupling via dual gold/photoredox catalysis.
Figure 43: Proposed mechanism for the undirected C–H aryl–aryl cross-coupling via dual catalysis.
Figure 44: Undirected C–H arylation of (hetero)arenes via dual manganese/photoredox catalysis.
Figure 45: Proposed mechanism for the undirected arylation of (hetero)arenes via dual catalysis.
Figure 46: Photoinduced C–H arylation of azoles via copper catalysis.
Figure 47: Photo-induced C–H chalcogenation of azoles via copper catalysis.
Figure 48: Decarboxylative C–H adamantylation of azoles via dual cobalt/photoredox catalysis.
Figure 49: Proposed mechanism for the C–H adamantylation of azoles via dual catalysis.
Figure 50: General mechanisms for the “classical” (left) and Cu-free variant (right) Sonogoshira reaction.
Figure 51: First example of a dual palladium/photoredox catalysis for Sonogashira-type couplings.
Figure 52: Arylation of terminal alkynes with diazonium salts via dual gold/photoredox catalysis.
Figure 53: Proposed mechanism for the arylation of terminal alkynes via dual catalysis.
Figure 54: C–H Alkylation of alcohols promoted by H-atom transfer (HAT).
Figure 55: Proposed mechanism for the C–H alkylation of alcohols promoted by HAT.
Figure 56: C(sp3)–H arylation of latent nucleophiles promoted by H-atom transfer.
Figure 57: Proposed mechanism for the C(sp3)–H arylation of latent nucleophiles promoted by HAT.
Figure 58: Direct α-arylation of alcohols promoted by H-atom transfer.
Figure 59: Proposed mechanism for the direct α-arylation of alcohols promoted by HAT.
Figure 60: C–H arylation of amines via dual Ni/photoredox catalysis.
Figure 61: Proposed mechanism for the C–H arylation of amines via dual Ni/photoredox catalysis.
Figure 62: C–H functionalization of nucleophiles via excited ketone/nickel dual catalysis.
Figure 63: Proposed mechanism for the C–H functionalization enabled by excited ketones.
Figure 64: Selective sp3–sp3 cross-coupling promoted by H-atom transfer.
Figure 65: Proposed mechanism for the selective sp3–sp3 cross-coupling promoted by HAT.
Figure 66: Direct C(sp3)–H acylation of amines via dual Ni/photoredox catalysis.
Figure 67: Proposed mechanism for the C–H acylation of amines via dual Ni/photoredox catalysis.
Figure 68: C–H hydroalkylation of internal alkynes via dual Ni/photoredox catalysis.
Figure 69: Proposed mechanism for the C–H hydroalkylation of internal alkynes.
Figure 70: Alternative procedure for the C–H hydroalkylation of ynones, ynoates, and ynamides.
Figure 71: Allylic C(sp3)–H activation via dual Ni/photoredox catalysis.
Figure 72: Proposed mechanism for the allylic C(sp3)–H activation via dual Ni/photoredox catalysis.
Figure 73: Asymmetric allylation of aldehydes via dual Cr/photoredox catalysis.
Figure 74: Proposed mechanism for the asymmetric allylation of aldehydes via dual catalysis.
Figure 75: Aldehyde C–H functionalization promoted by H-atom transfer.
Figure 76: Proposed mechanism for the C–H functionalization of aldehydes promoted by HAT.
Figure 77: Direct C–H arylation of strong aliphatic bonds promoted by HAT.
Figure 78: Proposed mechanism for the C–H arylation of strong aliphatic bonds promoted by HAT.
Figure 79: Direct C–H trifluoromethylation of strong aliphatic bonds promoted by HAT.
Figure 80: Proposed mechanism for the C–H trifluoromethylation of strong aliphatic bonds.
Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8
Graphical Abstract
Scheme 1: Pyrrole–imidazole–azobenzene polyamides and the dsDNA target sequences employed in this study.
Scheme 2: Building blocks required for the synthesis of the photoswitchable Im/Py polyamides. A) Fmoc–Azo–OH 1...
Figure 1: Section of the 1H NMR (600 MHz) spectrum of polyamide P1. A) Initial thermal equilibrium. B) After ...
Figure 2: E/Z isomer ratio of the polyamides P1–P3. Values were obtained from the respective 1H NMR experimen...
Figure 3: Titration experiments of target DNA sequences with P1–P3 in the photostationary Z-state and the the...
Figure 4: Titration of DNA containing single mutations (in bold) with P1–P3 in the photostationary Z-state an...
Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6
Graphical Abstract
Figure 1: DAE photoswitch and photoswitchable peptides explored in this study. (A) The reversible photoisomer...
Figure 2: Two versions of the D. rerio embryotoxicity assay for DAE-modified peptides: timelines, peptide pho...
Figure 3: The in vivo toxicity against D. rerio embryos appears to be correlated with the empirical hydrophob...
Figure 4: D. rerio embryotoxicity of GS 1 and the photoswitchable analogues 2–20 correlated with their in vit...
Figure 5: Phototherapeutic cytotoxic action against HeLa cells of GS 1 and its photoswitchable analogues 2–20...
Beilstein J. Org. Chem. 2019, 15, 52–59, doi:10.3762/bjoc.15.5
Graphical Abstract
Figure 1: Reduction potentials (vs SCE) of common photoredox catalysts, pyrene 16 and phenothiazine 2, in com...
Figure 2: Acceptor or donor-modified phenothiazines 1–11 as potential photoredox catalysts.
Figure 3: Normalized UV–vis absorption spectra above 290 nm of N-phenylphenothiazines 1–11 (left) and represe...
Figure 4: Proposed mechanism for the photoredox-catalyzed addition of methanol to α-methylstyrene (13a). (ET ...
Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163
Graphical Abstract
Figure 1: Principle of photoaffinity labeling of proteins with diazirine derivatives. Photolabile ligands are...
Figure 2: FimH crystal structure (pdb code 1KLF) with docked p-nitrophenyl α-D-mannopyranoside (1, pNPMan). F...
Figure 3: Based on the structure of the known FimH ligands 1 and 2, three photolabile α-D-mannosides, 3–5, we...
Figure 4: Connolly representation of photolabile α-D-mannoside 3 in the closed gate (A, PDB code 1UWF) and op...
Scheme 1: Synthesis of photolabile α-D-mannosides 3 and 4. a) H2, Pd-C, methanol, rt, 6 h, 94%; b) HATU, DIPE...
Figure 5: ESIMS spectra of peptide M2 before (A) and after photoreaction (B) with mannoside 3.
Figure 6: Intact protein ESIMS spectra of FimHtr labeling with diazirine derivative 3 with (A) 50% acetonitri...
Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32
Graphical Abstract
Scheme 1: Demasking under reducing agents of ON prodrugs modified as phosphotriesters with A) benzyl groups [13] ...
Scheme 2: A) Synthesis via phosphoramidite chemistry and B) demasking under the reducing environment of 2’-O-...
Scheme 3: Synthesis via phosphoramidite chemistry of various 2’-O-alkyldithiomethyl (RSSM)-modified RNAs bear...
Scheme 4: A) siRNA conjugates to cholesterol [19] and B) PNA conjugates to a triphenylphosphonium [20] through a disu...
Scheme 5: Synthesis via phosphoramidite chemistry and deprotection mediated by nitroreductase/NADH of hypoxia...
Scheme 6: Synthesis via phosphoramidite chemistry and conversion mediated by nitroreductase/NADH of hypoxia-a...
Scheme 7: Incorporation of O6-(4-nitrobenzyl)-2’-deoxyguanosine into an ON prone to form a G-quadruplex struc...
Scheme 8: Synthesis and mechanism for the demasking of ON prodrugs from A) S-acylthioethyl phosphotriester [29] a...
Figure 1: Oligothymidylates bearing A) 2,2-bis(ethoxycarbonyl)-3-(pivaloyloxy)propyl- and B) 2-cyano-2(2-phen...
Figure 2: Oligothymidylates containing esterase and thermo-labile (4-acetylthio-2,2-dimethyl-3-oxobutyl) phos...
Scheme 9: Phosphoramidites and the corresponding RNA prodrugs protected as A) t-Bu-SATE, B) OH-SATE and C) A-...
Scheme 10: Mechanism of the hydrolysis of 2’-O-acyloxymethyl ONs mediated by carboxyesterases [46]. The hydrolysis...
Scheme 11: Synthesis of partially 2’-O-PivOM-modified RNAs [49] and 2’-O-PiBuOM-modified RNAs [53] using their corresp...
Figure 3: A) 2’-O-amino and guanidino-containing acetal ester phosphoramidites and B) 2’-O-(amino acid) aceta...
Scheme 12: Prodrugs of tricyclo-ONs functionalized with A) ethyl (tcee-T) and B) hexadecyl (tchd-T) ester func...
Scheme 13: Demasking mechanism of fma thiophosphate triesters in CpG ODN upon heat action [58].
Scheme 14: Thermolytic cleavage of the hydroxy-alkylated thiophosphate and phosphato-/thiophosphato-alkylated ...
Scheme 15: Synthesis via phosphoramidite chemistry and thermolytic cleavage of alkylated (diisopropyl, diethyl...
Scheme 16: Synthesis of thermosensitive prodrugs of ODNs containing fma thiophosphate triesters combined to po...
Scheme 17: Caging of deoxycytidine in methylphosphonate ONs by using the thermolabile phenylsulfonylcarbamoyl ...
Figure 4: Biotinylated 1-(5-(aminomethyl)-2-nitrophenyl)ethyl phosphoramidite used to cage the 5’-end of a si...
Scheme 18: Introduction and cleavage of 1-(4,5-dimethoxy-2-nitrophenyl)ethyl (DMNPE) [74] and cyclododecyl-DMNPE (...
Scheme 19: Post-synthetic introduction of a thioether-enol phosphodiester (TEEP) linkage into a DNAzyme by the...
Scheme 20: A) NPP dT and dG phosphoramidites [91,92] and B) NPOM U and G phosphoramidites [83] used to introduce photocag...
Scheme 21: Introduction of the photocaged 3-NPOM nucleobase into phosphorothioate antisense and morpholino ant...
Scheme 22: Control of the activity of an antisense ODN using a photocaged hairpin [82]. Formation of the hairpin s...
Scheme 23: Control of alternative splicing using phosphorothioate (PS) 2’-OMe-photocaged ONs resulting from th...
Scheme 24: A) Light activation of a photocaged DNAzyme incorporating 3-NPOM thymidine in its catalytic site [87]; ...
Scheme 25: Incorporation of 3-(6-nitropiperonyloxymethyl) (NPOM) thymidine and 4-nitropiperonylethyl (NPE) deo...
Scheme 26: Synthesis of a photocaged DNA decoy from a 3-NPOM thymidine phosphoramidite and release of the NPOM...
Scheme 27: Synthesis of a caged DNA decoy hairpin containing a 7-nitroindole nucleotide and release of the mod...
Figure 5: Caged-2’-adenosines used by MacMillan et al [93,94] (X = O) and Piccirilli et al [95] (X = S) to study RNA mec...
Scheme 28: Synthesis of circular ODNs containing a photolabile linker as described by Tang et al. [101,104].
Scheme 29: Control of RNA digestion with RNase H using light activation of a photocaged hairpin [97].
Scheme 30: Photocontrol of RNA degradation using caged circular antisense ODNs containing a photoresponsive li...
Scheme 31: Control of RNA translation using an “RNA bandage” consisting of two short 2’-OMe ONs linked togethe...
Scheme 32: Control of alternative splicing using photocaged ONs resulting from the incorporation of an o-nitro...
Scheme 33: A) Light deactivation of a photocaged DNAzyme incorporating one photocleavable spacer in its cataly...
Scheme 34: Solid-phase synthesis of a caged vit E-siRNA conjugate and its release upon UV irradiation [106].
Scheme 35: Synthesis of a siRNA conjugated to a nanoparticle (NP) via a cyclooctene heterolinker from a siRNA-...
Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30
Graphical Abstract
Scheme 1: Mechanism for the reduction under metal dissolving conditions.
Scheme 2: Example of decyanation in metal dissolving conditions coupled with deprotection [30]. TBDMS = tert-buty...
Scheme 3: Preparation of α,ω-dienes [18,33].
Scheme 4: Cyclization reaction using a radical probe [18].
Scheme 5: Synthesis of (±)-xanthorrhizol (8) [39].
Scheme 6: Mechanism for the reduction of α-aminonitriles by hydride donors.
Scheme 7: Synthesis of phenanthroindolizidines and phenanthroquinolizidines [71].
Scheme 8: Two-step synthesis of 5-unsubstituted pyrrolidines (25 examples and 1 synthetic application, see be...
Scheme 9: Synthesis of (±)-isoretronecanol 19. DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene [74].
Scheme 10: Proposed mechanism with 14a for the NaBH4 induced decyanation reaction (“BH3” = BH3·THF) [74].
Scheme 11: Reductive decyanation by a sodium hydride–iodide composite (26 examples) [81].
Scheme 12: Proposed mechanism for the reduction by NaH [81].
Scheme 13: Reductive decyanation catalyzed by nickel nanoparticles. Yields are given in weight % from GC–MS da...
Scheme 14: Decyanation of 2-cyanobenzo[b]thiophene [87].
Scheme 15: Simplified pathways involved in transition-metal-promoted reductive decyanations [93,95].
Scheme 16: Fe-catalyzed reductive decyanation. Numbers in square brackets represent turnover numbers. The TONs...
Scheme 17: Rh-catalyzed reductive decyanation of aryl nitriles (18 examples, 2 synthetic applications) [103].
Scheme 18: Rh-catalyzed reductive decyanation of aliphatic nitriles (15 examples, one synthetic application) [103].
Scheme 19: Ni-catalyzed reductive decyanation (method A: 28 examples and 2 synthetic applications; method B: 3...
Scheme 20: Reductive decyanation catalyzed by the nickel complex 58 (method A, 14 examples, yield ≥ 20% and 1 ...
Scheme 21: Proposed catalytic cycle for the nickel complex 58 catalyzed decyanation (method A). Only the cycle...
Scheme 22: Synthesis of bicyclic lactones [119,120].
Scheme 23: Reductive decyanation of malononitriles and cyanoacetates using NHC-boryl radicals (9 examples). Fo...
Scheme 24: Proposed mechanism for the reduction by NHC-boryl radicals. The other possible pathway (addition of ...
Scheme 25: Structures of organic electron-donors. Only the major Z isomer of 80 is shown [125,127].
Scheme 26: Reductive decyanation of malononitriles and cyanoacetates using organic electron-donors (method A, ...
Scheme 27: Photoreaction of dibenzylmalononitrile with 81 [128].
Scheme 28: Examples of decyanation promoted in acid or basic media [129,131,134,135].
Scheme 29: Mechanism proposed for the base-induced reductive decyanation of diphenylacetonitriles [136].
Scheme 30: Reductive decyanation of triarylacetonitriles [140].
Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248
Graphical Abstract
Figure 1: Schematic representation of adamantane-substituted squaraine (AdSq) binding as a divalent guest to ...
Figure 2: Absorption spectra of AdSq in acetonitrile. [AdSq] = 7.5 µM. Top: Absorption at different time poin...
Figure 3: Top: Emission spectra (ex: 630 nm) of AdSq immobilized at CDV. [CDV] = 0–100 µM; [AdSq] = 5 µM. Bot...
Figure 4: Confocal fluorescence microscopy of giant unilamellar vesicles (GUVs) of amphiphilic cyclodextrins ...
Figure 5: Top: Absorption spectra at different time points during irradiation of a CDV solution with AdSq imm...
Figure 6: Synthesis of AdSq (I) NaH, DMF, 1,6-dibromohexane, 24 h, rt. (II) benzothiazole, acetonitrile, 12 h...
Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173
Graphical Abstract
Figure 1: Production and utilization of h+ and e– by photoactivation of a semiconductor.
Figure 2: Photoredox activity of TiO2 with moist air.
Scheme 1: TiO2 promoted oxidation of phenanthrene [29].
Scheme 2: SCPC assisted additions of allylic compounds to diazines and imines [40-42].
Scheme 3: TiO2 promoted addition and addition–cyclization reactions of tert-amines with electron-deficient al...
Scheme 4: Reactions of amines promoted by Pt-TiO2 [48,49].
Scheme 5: P25 Promoted alkylations of N-phenylmaleimide with diverse carboxylic acids [53,54]. aAccompanied by R–R d...
Scheme 6: SCPC cyclizations of aryloxyacetic acids with suitably sited alkene acceptors [54]. aYields in brackets...
Scheme 7: TiO2 promoted reactions of aryloxyacetic acids with maleic anhydride and maleimides [53,54].
Scheme 8: Photoredox addition–cyclization reactions of aryloxyacetic and related acids promoted by maleimide [63]....
Scheme 9: SCPC promoted homo-couplings and macrocyclizations with carboxylic acids [64].
Scheme 10: TiO2 promoted alkylations of alkenes with silanes [66] and thiols [67].
Scheme 11: TiO2 reduction of a nitrochromenone derivative [70].
Scheme 12: TiO2 mediated hydrodehalogenations and cyclizations of organic iodides [71].
Scheme 13: TiO2 promoted hydrogenations of maleimides, maleic anhydride and aromatic aldehydes [79].
Scheme 14: Mechanistic sketch of SCPC hydrogenation of aryl aldehydes.
Beilstein J. Org. Chem. 2014, 10, 2981–2988, doi:10.3762/bjoc.10.316
Graphical Abstract
Figure 1: Examples of biologically active 1,2-disubstituted tetrahydroisoquinolines.
Scheme 1: Oxidative C–H functionalisation and examples of previously reported nucleophilic trappings.
Figure 2: Products from allylzinc reagent addition to 5a and 5b.
Figure 3: Proposed mechanism for formation of side-product 8a. Analogous reactivity in the formation of cycli...
Figure 4: Mechanism for dimerisation of the allylzinc halide and β-hydride addition to 5a [36].
Scheme 2: A concise synthesis of methopholine (3).
Beilstein J. Org. Chem. 2013, 9, 1745–1750, doi:10.3762/bjoc.9.201
Graphical Abstract
Scheme 1: Formation of azirines 2 from vinyl azides 1, photoinduced ring-opening to the nitrile ylides 3, and...
Scheme 2: Solid-phase assisted synthesis of vinyl azides 1 from alkenes 6 under flow conditions [9].
Scheme 3: Schematic presentation of the flow set-up for the synthesis of 2H-azirines 2 under inductive heatin...
Scheme 4: Photoinduced cycloadditions of vinyl azides 1a–f and electron-deficient alkenes 4a–d. All experimen...
Scheme 5: Photoinduced cycloaddtion of vinyl azide 1c and diisopropyl azodicarboxylate (4e). The experiment w...
Scheme 6: Photoinduced cycloaddtion of vinyl azide 1b and alkyne 4f. The experiment was conducted at room tem...
Scheme 7: Formation of 2,5-dihydrooxazole 9 starting from vinyl azide 1g under flow conditions (c = 0.01 M, f...
Beilstein J. Org. Chem. 2013, 9, 64–73, doi:10.3762/bjoc.9.8
Graphical Abstract
Figure 1: Structures of various caging chromophores. Abbreviations: Noc, N-nitrophenethyloxycarbonyl; CNB, ca...
Figure 2: Comparative two-photon uncaging of MNI-Glu and CDNI-Glu on pyramidal neurons in an acutely isolated...
Beilstein J. Org. Chem. 2011, 7, 813–823, doi:10.3762/bjoc.7.93
Graphical Abstract
Figure 1: Structure of C-lysine conjugates.
Figure 2: Alternative pathways of enediyne photoreactivity: photo-Bergman cyclization (left), C1–C5 cyclizati...
Figure 3: Summary of possible mechanistic alternatives for the observed DNA cleavage by monoacetylene conjuga...
Scheme 1: Proposed mechanism of photocycloaddition of acetylene with 1,4-CHD.
Figure 4: p-, m-, and o-amidyl acetylenes and respective lysine conjugates.
Scheme 2: Synthesis of amido-substituted monoacetylenes and lysine conjugates. Reagents and conditions: a. Pd...
Scheme 3: Photochemical reactions of TFP-substituted aryl alkynes with selected π-systems. In short, the reac...
Scheme 4: Photocycloaddition of amido acetylenes with 1,4-CHD.
Scheme 5: Possible mechanism for photochemical hydration of diaryl acetylene moiety catalyzed by the ortho-am...
Figure 5: Stern–Volmer plots of three regioisomers, 3 (blue diamond), 4 (red square), and 5 (green triangle),...
Figure 6: Absorption spectra of three isomers, 3, 4, 5, and Ph-TFP in acetonitrile (10 μM).
Figure 7: Quantified DNA cleavage data for 1 (a), 6 (b) and 7 (c). Blue: Form I (supercoiled) DNA; red: Form ...
Figure 8: Effect of hydroxyl radical/singlet oxygen scavengers (20 mM) on the efficiency of DNA cleavage at p...
Figure 9: Cell proliferation assay using A375 cells (human melanoma) and compound 1 (green square), 6 (red up...
Beilstein J. Org. Chem. 2010, 6, 1106–1119, doi:10.3762/bjoc.6.127
Graphical Abstract
Scheme 1: Light activated metathesis of trans-2-pentene.
Scheme 2: Light induced generation of metathesis active species 2.
Figure 1: Well-defined tungsten photoactive catalysts.
Figure 2: The first ruthenium based complexes for PROMP.
Figure 3: Cyclic strained alkenes for PROMP.
Scheme 3: Proposed mechanism for photoactivation of sandwich complexes.
Figure 4: Ruthenium and osmium complexes with p-cymene and phosphane ligands for PROMP.
Figure 5: Commercially available photoactive ruthenium precatalyst.
Figure 6: Some of the rings produced by photo-RCM.
Scheme 4: Photopromoted ene-yne RCM by cationic allenylidene ruthenium complex 14.
Figure 7: Dihydrofurans synthesised by photopromoted ene-yne RCM.
Figure 8: Ruthenium complexes with p-cymene and NHC ligands.
Scheme 5: Ruthenium NHC complexes for PROMP containing p-cymene and trifluroacetate (17, 19) or phenylisonitr...
Figure 9: Photoactivated cationic ROMP precatalysts.
Figure 10: Different monomers for PROMP.
Scheme 6: Proposed mechanism for photoinitiated polymerisation by 22 and 23.
Figure 11: Light-induced cationic catalysts for ROMP.
Figure 12: Sulfur chelated ruthenium benzylidene pre-catalysts for olefin metathesis.
Scheme 7: Proposed mechanism for the photoactivation of sulfur-chelated ruthenium benzylidene.
Figure 13: Photoacid generators for photoinduced metathesis.
Scheme 8: Synthesis of precatalysts 36 and 37.
Scheme 9: Trapping of proposed intermediate 41.
Figure 14: Encapsulated 39, isolated from the monomer.