Search results
Search for "multiple bond" in Full Text gives 29 result(s) in Beilstein Journal of Organic Chemistry.
Amines as key building blocks in Pd-assisted multicomponent processes
- Didier Bouyssi,
- Nuno Monteiro and
- Geneviève Balme
Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163
- coupling of aryl chlorides. This was followed by an intramolecular alkyne–hydroamination (addition of an N–H bond across a carbon–carbon multiple bond) leading to the corresponding indole derivatives 52. The amination/alkyne–hydroamination sequence requires the addition of 1.5 equiv of t-BuOK to reach
Graphical Abstract
Scheme 1: Synthesis of substituted amides.
Scheme 2: Synthesis of ketocarbamates and imidazolones.
Scheme 3: Access to β-lactams.
Scheme 4: Access to β-lactams with increased structural diversity.
Scheme 5: Synthesis of imidazolinium salts.
Scheme 6: Access to the indenamine core.
Scheme 7: Synthesis of substituted tetrahydropyridines.
Scheme 8: Synthesis of more substituted tetrahydropyridines.
Scheme 9: Synthesis of chiral tetrahydropyridines.
Scheme 10: Preparation of α-aminonitrile by a catalyzed Strecker reaction.
Scheme 11: Synthesis of spiroacetals.
Scheme 12: Synthesis of masked 3-aminoindan-1-ones.
Scheme 13: Synthesis of homoallylic amines and α-aminoesters.
Scheme 14: Preparation of 1,2-dihydroisoquinolin-1-ylphosphonates.
Scheme 15: Pyrazole elaboration by cycloaddition of hydrazines with alkynones generated in situ.
Scheme 16: An alternative approach to pyrazoles involving hydrazine cycloaddition.
Scheme 17: Synthesis of pyrroles by cyclization of propargyl amines.
Scheme 18: Isoindolone and phthalazone synthesis by cyclization of acylhydrazides.
Scheme 19: Sultam synthesis by cyclization of sulfonamides.
Scheme 20: Synthesis of sulfonamides by aminosulfonylation of aryl iodides.
Scheme 21: Pyrrolidine synthesis by carbopalladation of allylamines.
Scheme 22: Synthesis of indoles through a sequential C–C coupling/desilylation–coupling/cyclization reaction.
Scheme 23: Synthesis of indoles by a site selective Pd/C catalyzed cross-coupling approach.
Scheme 24: Synthesis of isoindolin-1-one derivatives through a sequential Sonogashira coupling/carbonylation/h...
Scheme 25: Synthesis of pyrroles through an allylic amination/Sonogashira coupling/hydroamination reaction.
Scheme 26: Synthesis of indoles through a Sonogashira coupling/cyclofunctionalization reaction.
Scheme 27: Synthesis of indoles through a one-pot two-step Sonogashira coupling/cyclofunctionalization reactio...
Scheme 28: Synthesis of α-alkynylindoles through a Pd-catalyzed Sonogashira/double C–N coupling reaction.
Scheme 29: Synthesis of indoles through a Pd-catalyzed sequential alkenyl amination/C-arylation/N-arylation.
Scheme 30: Synthesis of N-aryl-2-benzylpyrrolidines through a sequential N-arylation/carboamination reaction.
Scheme 31: Synthesis of phenothiazine derivatives through a one-pot palladium-catalyzed double C–N arylation i...
Scheme 32: Synthesis of substituted imidazolidinones through a palladium-catalyzed three-component reaction of...
Scheme 33: Synthesis of 2,3-diarylated amines through a palladium-catalyzed four-component reaction involving ...
Scheme 34: Synthesis of rolipram involving a Pd-catalyzed three-component reaction.
Scheme 35: Synthesis of seven-membered ring lactams through a Pd-catalyzed amination/intramolecular cyclocarbo...
Multicomponent reaction access to complex quinolines via oxidation of the Povarov adducts
- Esther Vicente-García,
- Rosario Ramón,
- Sara Preciado and
- Rodolfo Lavilla
Beilstein J. Org. Chem. 2011, 7, 980–987, doi:10.3762/bjoc.7.110
- single quantum coherence) and long-range 1H,13C-COSY (HMBC: heteronuclear multiple bond connectivity). IR spectra were recorded using a Thermo Nicolet Nexus spectrometer and are reported in wavenumbers (cm−1). High resolution mass spectrometry was performed by the University of Barcelona Mass
Graphical Abstract
Scheme 1: Povarov oxidation access to substituted quinolines.
Scheme 2: Tetrahydroquinoline oxidation.
Scheme 3: Synthesis of the Povarov adducts and their oxidation products.
Figure 1: Optimization of the reaction conditions for the preparation of quinoline 18.
Scheme 4: Oxidation of lactam-fused tetrahydroquinolines 20,20'.
Recent advances in the gold-catalyzed additions to C–C multiple bonds
- He Huang,
- Yu Zhou and
- Hong Liu
Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103
- catalytic addition of a nitrogen nucleophile to a C–C multiple bond represents an attractive approach to the formation of C–N bonds [55]. This is a direct and efficient procedure for the synthesis of nitrogen containing compounds of industrial importance. 3.1 Alkyl- and aromatic amines as nucleophiles
Graphical Abstract
Scheme 1: Gold-catalyzed addition of alcohols.
Scheme 2: Gold-catalyzed cycloaddition of alcohols.
Scheme 3: Ionic liquids as the solvent in gold-catalyzed cycloaddition.
Scheme 4: Gold-catalyzed cycloaddition of diynes.
Scheme 5: Gold(I) chloride catalyzed cycloisomerization of 2-alkynyl-1,5-diols.
Scheme 6: Gold-catalyzed cycloaddition of glycols and dihydroxy compounds.
Scheme 7: Gold-catalyzed ring-opening of cyclopropenes.
Scheme 8: Gold-catalyzed intermolecular hydroalkoxylation of alkynes. PR3 = 41–45.
Scheme 9: Gold-catalyzed intramolecular 6-endo-dig cyclization of β-hydroxy-α,α-difluoroynones.
Scheme 10: Gold-catalyzed intermolecular hydroalkoxylation of non-activated olefins.
Scheme 11: Preparation of unsymmetrical ethers from alcohols.
Scheme 12: Expedient synthesis of dihydrofuran-3-ones.
Scheme 13: Catalytic approach to functionalized divinyl ketones.
Scheme 14: Gold-catalyzed glycosylation.
Scheme 15: Gold-catalyzed cycloaddition of aldehydes and ketones.
Scheme 16: Gold-catalyzed annulations of 2-(ynol)aryl aldehydes and o-alkynyl benzaldehydes.
Scheme 17: Gold-catalyzed addition of carboxylates.
Scheme 18: Dual-catalyzed rearrangement reaction of allenoates.
Scheme 19: Meyer–Schuster rearrangement of propargylic alcohols.
Scheme 20: Propargylic alcohol rearrangements.
Scheme 21: Gold-catalyzed synthesis of imines and amine alkylation.
Scheme 22: Hydroamination of allenes and allenamides.
Scheme 23: Gold-catalyzed inter- and intramolecular amination of alkynes and alkenes.
Scheme 24: Gold-catalyzed cycloisomerization of O-propioloyl oximes and β-allenylhydrazones.
Scheme 25: Intra- and intermolecular amination with ureas.
Scheme 26: Gold-catalyzed cyclization of ortho-alkynyl-N-sulfonylanilines and but-3-yn-1-amines.
Scheme 27: Gold-catalyzed piperidine ring synthesis.
Scheme 28: Ring expansion of alkylnyl cyclopropanes.
Scheme 29: Gold-catalyzed annulations of N-propargyl-β-enaminones and azomethine imines.
Scheme 30: Gold(I)-catalyzed cycloisomerization of aziridines.
Scheme 31: AuCl3/AgSbF6-catalyzed intramolecular amination of 2-(tosylamino)phenylprop-1-en-3-ols.
Scheme 32: Gold-catalyzed cyclization via a 7-endo-dig pathway.
Scheme 33: Gold-catalyzed synthesis of fused xanthines.
Scheme 34: Gold-catalyzed synthesis of amides and isoquinolines.
Scheme 35: Gold-catalyzed oxidative cross-coupling reactions of propargylic acetates.
Scheme 36: Gold-catalyzed nucleophilic addition to allenamides.
Scheme 37: Gold-catalyzed direct carbon–carbon bond coupling reactions.
Scheme 38: Gold-catalyzed C−H functionalization of indole/pyrrole heterocycles and non-activated arenes.
Scheme 39: Gold-catalyzed cycloisomerization of cyclic compounds.
Scheme 40: Gold-catalyzed cycloaddition of 1-aryl-1-allen-6-enes and propargyl acetates.
Scheme 41: Gold(I)-catalyzed cycloaddition with ligand-controlled regiochemistry.
Scheme 42: Gold(I)-catalyzed cycloaddition of dienes and enynes.
Scheme 43: Gold-catalyzed intramolecular cycloaddition of 3-alkoxy-1,5-enynes and 2,2-dipropargylmalonates.
Scheme 44: Gold-catalyzed intramolecular cycloaddition of 1,5-allenynes.
Scheme 45: Gold(I)-catalyzed cycloaddition of indoles.
Scheme 46: Gold-catalyzed annulation reactions.
Scheme 47: Gold–carbenoid induced cleavage of a sp3-hybridized C−H bond.
Scheme 48: Furan- and indole-based cascade reactions.
Scheme 49: Tandem process using aromatic alkynes.
Scheme 50: Gold-catalyzed cycloaddition of 1,3-dien-5-ynes.
Scheme 51: Gold-catalyzed cascade cyclization of diynes, propargylic esters, and 1,3-enynyl ketones.
Scheme 52: Tandem reaction of β-phenoxyimino ketones and alkynyl oxime ethers.
Scheme 53: Gold-catalyzed tandem cyclization of enynes, 2-(tosylamino)phenylprop-1-yn-3-ols, and allenoates.
Scheme 54: Cyclization of 2,4-dien-6-yne carboxylic acids.
Scheme 55: Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolines.
Scheme 56: Gold-catalyzed tandem reactions of alkynes.
Scheme 57: Aminoarylation and oxyarylation of alkenes.
Scheme 58: Cycloaddition of 2-ethynylnitrobenzene with various alkenes.
Scheme 59: Gold-catalyzed tandem reactions of allenoates and alkynes.
Scheme 60: Gold-catalyzed asymmetric synthesis of 2,3-dihydropyrroles.
Scheme 61: Chiral [NHC–Au(I)]-catalyzed cyclization of enyne.
Scheme 62: Gold-catalyzed hydroaminations and hydroalkoxylations.
Scheme 63: Gold(I)-catalyzed asymmetric hydroalkoxylation of 1,3-dihydroxymethyl-2-alkynylbenzene chromium com...
Scheme 64: Gold-catalyzed synthesis of julolidine derivatives.
Scheme 65: Gold-catalyzed the synthesis of chiral fused heterocycles.
Scheme 66: Gold-catalyzed asymmetric reactions with 3,5-(t-Bu)2-4-MeO-MeOBIPHEP.
Scheme 67: Gold-catalyzed cyclization of o-(alkynyl) styrenes.
Scheme 68: Asymmetric gold(I)-catalyzed redox-neutral domino reactions of enynes.
Scheme 69: Gold(I)-catalyzed enantioselective polyene cyclization reaction.
Scheme 70: Gold(I)-catalyzed enantioselective synthesis of benzopyrans.
Scheme 71: Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.
The catalytic performance of Ru–NHC alkylidene complexes: PCy3 versus pyridine as the dissociating ligand
- Stefan Krehl,
- Diana Geißler,
- Sylvia Hauke,
- Oliver Kunz,
- Lucia Staude and
- Bernd Schmidt
Beilstein J. Org. Chem. 2010, 6, 1188–1198, doi:10.3762/bjoc.6.136
- if the pyridine complex H is used as a catalyst. For other examples, we have previously observed that benzyl ether moieties in close proximity to a C–C-multiple bond retard or inhibit metathesis reactions [50]. Presumably, partial catalyst deactivation by coordination of the benzyloxy group to the
Graphical Abstract
Figure 1: Ru-based metathesis catalysts.
Scheme 1: RCM of an allyl ether catalyzed by catalyst H.
Figure 2: Solvent screening for the RCM of 1 catalyzed by H (standardized conditions as denoted in Scheme 1).
Figure 3: Comparison of catalysts D, E and H in toluene and acetic acid (standardized conditions as denoted i...
Figure 4: Conversion vs catalyst loading for the RCM of 1 in acetic acid (standardized conditions as denoted ...
Scheme 2: Catalyst screening for RCM of acrylate 3a.
Figure 5: Acrylates 3 and their RCM products 4.
Scheme 3: Ring closing enyne metathesis reactions.
Scheme 4: Cross metathesis reactions with allylic alcohol 8.
