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Search for "alkynes" in Full Text gives 455 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

  • Andrew D. Gillie,
  • Matthew G. Wakeling,
  • Bethan L. Greene,
  • Louise Male and
  • Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

Graphical Abstract
  • seen with imidazolidines (cf. for IPr TEP[Ir] = 2050.2 cm−1) [34]. A benchmarking exercise was then performed looking at the reactivity of 13 compared against reaction of symmetrical IPrAuCl across a range of known gold-mediated transformations of alkynes featuring intermolecular attack [35
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Published 18 Mar 2024

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

  • Ruichen Lan,
  • Brock Yager,
  • Yoonsun Jee,
  • Cynthia S. Day and
  • Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

Graphical Abstract
  • Since the seminal 1998 report by Teles et al. on the gold(I)-catalyzed addition of alcohols to alkynes [1], a multitude of gold-catalyzed reactions have been reported. Great successes in mechanistic analysis and synthetic methods have been achieved for allene and alkyne activation, while the activation
  • ) protodeauration (Scheme 1), the depth of experimental mechanistic validation achieved for allenes and alkynes have not been reproduced with alkenes. In an important foundational study by Toste, the expected alkylgold intermediate from intramolecular alkene hydroamination was isolated, however, turnover
  • solvent and anion effects add complexity to mechanistic interpretation, and the reluctance of alkylgold complexes to undergo protodeauration under similar conditions give us pause [28]. While computational studies support protodeauration, the significantly lower reactivity of alkenes compared to alkynes
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Published 29 Feb 2024

Nucleophilic functionalization of thianthrenium salts under basic conditions

  • Xinting Fan,
  • Duo Zhang,
  • Xiangchuan Xiu,
  • Bin Xu,
  • Yu Yuan,
  • Feng Chen and
  • Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

Graphical Abstract
  • generation of alkyl radicals [39]. After that, a series of methods for the modification of alkylthianthrenium salts have been developed, including the transition-metal-catalyzed cross-coupling with terminal alkynes [40], sulfonylation with DABCO·(SO2)2 [41][42][43], or alkylation of active alkenes [44][45
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Published 08 Feb 2024

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

  • Ekaterina V. Kolupaeva,
  • Narek A. Dzhangiryan,
  • Alexander F. Pozharskii,
  • Oleg P. Demidov and
  • Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

Graphical Abstract
  • formation of unsaturated products, often in the form of polyenes or alkynes [28]. The non-standard transition method found here in the acenaphthene–acenaphthylene pair is a previously unknown approach for the synthesis of acenaphthylenes based on tele-elimination (see also below). Changing the nucleophile
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Published 08 Feb 2024
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  • ) reactions involving diverse electron-rich alkynes and electron-deficient alkenes. In this review, a comprehensive investigation of the recent and noteworthy advancements in the research on push–pull chromophores prepared via the [2 + 2] CA–RE reaction is conducted. In particular, an overview of the
  • optoelectronics) [1][2]. The synthesis of push–pull chromophores is often achieved through click-type reactions between electron-rich alkynes and electron-deficient alkenes, which is a reliable and atom-economical method. Diverse chromophores can be obtained via this method, depending upon the choice of alkynes
  • have explored the synthesis of various push–pull chromophores, primarily via reactions between alkynes and alkenes. Several comprehensive reviews of nonplanar push–pull chromophores have since enriched the scientific literature [4][5][6]. In 2018, Michinobu and Diederich provided an exemplary overview
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Published 22 Jan 2024

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

  • Christina Schøttler,
  • Kasper Lund-Rasmussen,
  • Line Broløs,
  • Philip Vinterberg,
  • Ema Bazikova,
  • Viktor B. R. Pedersen and
  • Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

Graphical Abstract
  • a subsequent Glaser–Hay coupling reaction, a RA acceptor unit was introduced to provide a DTF-IF-RA donor–acceptor scaffold with a low-energy charge-transfer absorption and multi-redox behavior. Keywords: alkynes; chromophores; fused-ring systems; heterocycles; redox chemistry; Introduction
  • , ethynylbenzene, or 4-ethynylbenzonitrile yielded compounds 19–21, while two-fold Sonogashira coupling with ((2-ethynylphenyl)ethynyl)triisopropylsilane resulted in compound 22. Desilylation of the alkynes of compound 22 with tetrabutylammonium fluoride (TBAF) and subsequent intramolecular Glaser–Hay coupling of
  • the terminal alkynes afforded the macrocyclic DTF-IF-RA scaffold 23. Molecular sieves (4 Å) were added to the reaction mixture as this has previously been shown to significantly promote the Glaser–Hay coupling [28]. Compounds 20 and 21 were unfortunately very sensitive compounds that were found to
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Published 15 Jan 2024

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF3: the case of alkyne hydration. Chemistry vs electrochemistry

  • Marta David,
  • Elisa Galli,
  • Richard C. D. Brown,
  • Marta Feroci,
  • Fabrizio Vetica and
  • Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

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  • , UK Department of Chemistry, Sapienza University of Rome, piazzale Aldo Moro, 5, 00185 Rome, Italy 10.3762/bjoc.19.147 Abstract In order to replace the expensive metal/ligand catalysts and classic toxic and volatile solvents, commonly used for the hydration of alkynes, the hydration reaction of
  • alkynes was studied in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate (BMIm-BF4) adding boron trifluoride diethyl etherate (BF3·Et2O) as catalyst. Different ionic liquids were used, varying the cation or the anion, in order to identify the best one, in terms of both efficiency and reduced
  • costs. The developed method was efficaciously applied to different alkynes, achieving the desired hydration products with good yields. The results obtained using a conventional approach (i.e., adding BF3·Et2O) were compared with those achieved using BF3 electrogenerated in BMIm-BF4, demonstrating the
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Published 28 Dec 2023

Biphenylene-containing polycyclic conjugated compounds

  • Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

Graphical Abstract
  • through Sonogashira cross-coupling reactions with alkynes featuring different protecting groups such as TIPS, TES, and TIBS. Scheme 7 illustrates the derivatization process using one of the chosen examples, specifically the TIPS group. Accordingly, the cross-coupling products 33a–c were obtained in yields
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Published 13 Dec 2023

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

  • Yordanka Mollova-Sapundzhieva,
  • Plamen Angelov,
  • Danail Georgiev and
  • Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

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  • of methods for their synthesis is a very active area of research. Recent contributions to the synthesis of 4-quinolones made use of phosphine-mediated redox cyclization of 1-(2-nitroaryl)prop-2-ynones [39], palladium-catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes [40], TsCl
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Published 23 Nov 2023

Lewis acid-promoted direct synthesis of isoxazole derivatives

  • Dengxu Qiu,
  • Chenhui Jiang,
  • Pan Gao and
  • Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

Graphical Abstract
  • nitrogen source (Scheme 1, reaction 2). In 2017, Xu and co-workers [19] developed a copper-mediated annulation reaction to synthesize isoxazoles from two different alkynes. In fact, most methods mostly used highly toxic transition-metal catalysts such as copper metals. In order to develop cheaper and more
  • environmentally friendly catalysts, our laboratory recently developed an alternative approach to the synthesis of isooxazoles starting from 2-methylquinoline and alkynes mediated by Brønsted acids in good yields (Scheme 1, reaction 3) [20]. The utilization of main element metal aluminum salts in organic synthesis
  • 11). With the optimal reaction conditions in hand, various alkynes were examined as dipolarophiles (Scheme 2). A range of functional groups were tolerated in this reaction, such as alkyl, methoxy, halo, and heterocycles. It was found that electron-deficient groups in the phenyl ring (3g–i) were more
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Published 16 Oct 2023

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

  • Tzu-Yu Huang,
  • Mario Djugovski,
  • Sweta Adhikari,
  • Destinee L. Manning and
  • Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

Graphical Abstract
  • azides without the requirement of alkynes or late-stage modifications. Our initial investigations led us to identify that adding morpholine as a solvent (0.34–0.4 M) in a reaction with 1-(2,2-difluoroethenyl)-4-methylbenzene (1 equiv) and phenyl azide (1.5 equiv) results in the formation of morpholine
  • with an organic azide. A relatively wide range of 1,4,5-trisubstituted-1,2,3-triazoles was obtained in 30–70% yields with high regioselectivity and modest functional group tolerability. This work demonstrates that gem-difluoroalkenes can serve as versatile fluorinated building blocks in lieu of alkynes
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Published 05 Oct 2023

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • of organic compounds, N-(alkyl/arylthio)phthalimides are also considered good candidates for this purpose. In 2017, Sahoo and co-workers established a method for intramolecular annulation of N-(arylthio)phthalimides 14 and N-(arylthio)succinimides 1 with alkynes 15 in the presence of AlCl3 as an
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Published 27 Sep 2023

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

  • Angel Palillero-Cisneros,
  • Paola G. Gordillo-Guerra,
  • Fernando García-Alvarez,
  • Olivier Jackowski,
  • Franck Ferreira,
  • Fabrice Chemla,
  • Joel L. Terán and
  • Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

Graphical Abstract
  • wherein the intermediate enoxyl radical II arising from the addition step evolves via intramolecular addition to tethered alkenes [16][17] or alkynes [18]. We wondered if, in the absence of the pending radical acceptor, the presence of the β-nitrogen atom could nevertheless promote zinc enolate formation
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Published 21 Sep 2023

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

  • Nosheen Beig,
  • Varsha Goyal and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

Graphical Abstract
  • + 2] cycloaddition of azides with alkynes as will be discussed later. Jin Zhang et al. used the same base, namely KOt-Bu in the presence of CuCl to obtain the thiazolylidene–Cu(I) complex 20 (Scheme 10) [23]. In 2012, Zhu and co-workers synthesized NHC–CuCl complexes using alkali carbonates (Na2CO3
  • yield by reacting [Cu(CH3CN)4]BF4 with 2 equiv of benzimidazolium salt 38 in the presence of NaOt-Bu (Scheme 14) [28]. The catalytic activity of the complex 39 was studied in the [3 + 2] cycloaddition of azides with alkynes [28]. Coyle et al. reported the synthesis of a series of NHC and ADC (acyclic
  • which showed that all complexes adopted a slightly distorted linear geometry. Furthermore, abnormal-NHC and triazolylidene-based Cu(I) complexes exhibited an outstanding catalytic property towards the [3 + 2] cycloaddition of alkynes with azides. Recently, we have reported the synthesis of NHC
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Published 20 Sep 2023

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

  • Hans-Ulrich Reissig and
  • Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

Graphical Abstract
  • azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis
  • carbohydrate mimetics, but the reductive cleavage of the 1,2-oxazine rings to aminopyran moieties did not proceed cleanly with these compounds. Keywords: alkynes; azides; copper catalysis; nucleophilic substitution; 1,2-oxazines; Introduction The concept of click reactions [1][2], in particular, the
  • ]). Mechanistic aspects of the CuAAC have been studied in detail [16][17]. Whereas the traditional 1,3-dipolar cycloaddition (Huisgen reaction) [18][19][20] of azides and alkynes requires often – but not always – relatively harsh conditions and proceeds with moderate regioselectivity only [21], the copper
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Published 18 Sep 2023

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

  • Nadia Ledermann,
  • Alae-Eddine Moubsit and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

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  • generated by a consecutive four-component reaction starting from ortho-haloanilines, terminal alkynes, N-iodosuccinimide, and alkyl halides in yields of 11–69%. Initiated by a copper-free alkynylation, followed by a base-catalyzed cyclizive indole formation, electrophilic iodination, and finally
  • -catalyzed processes for accessing indoles have become attractive alternatives over the past decades [19][20][21][22][23][24]. Besides Larock's indole synthesis employing alkyne anellation [25] and Cacchi's cyclization of ortho-alkynylanilines [20][22] catalytic syntheses of indoles from alkynes have become
  • to directly employ these standard conditions to the sequence of ortho-haloanilines 1, terminal alkynes 2, N-iodosuccinimide (3), and alkyl halides 4 to screen the scope of the one-pot synthesis of trisubstituted 3-iodoindoles 5 in a consecutive four-component fashion (Scheme 2). The sequence
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Published 14 Sep 2023

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds

  • Hui Yu and
  • Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

Graphical Abstract
  • terminal alkynes at room temperature (Scheme 15a) [67]. The ability to tune the reactivity of the trityl ion rationally improves the approach with excellent regio- and diastereoselectivity for the unsymmetric ethers. In 2018, Ye et al. reported a CDC reaction to form C(sp)–C(sp3) coupling products from
  • to afford internal alkynes from substrates with the C(sp3)–H bond mainly located in the α-position to N, O, or S atoms. This method provides a direct and atom-economical alternative for the construction of structurally complex alkyne compounds (Scheme 26) [87]. In addition to iron, various other
  •  27) [88]. This route provides an environmentally friendly and practical approach to alkyl-substituted alkynes. Co-catalyzed reactions In recent years, cobalt has exhibited great application potential as a cross-dehydrogenation coupling catalyst due to its low price, environmentally friendliness, and
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Published 06 Sep 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Graphical Abstract
  • pathways, respectively (Figure 20A). Both protocols were able to successfully engage perfluoroalkyl iodides and bromotrichloromethane in combination with a diverse scope of alkenes and alkynes (Figure 20B). Products of terminal alkenes and alkynes were generally obtained in good to excellent yields while
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Published 28 Jul 2023

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

  • Xiu-Yu Chen,
  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

Graphical Abstract
  • ]. The well-known Huisgen 1,4-dipoles have a special kind of zwitterionic intermediates and are usually prepared by a nucleophilic addition of pyridine, quinoline, isoquinoline and other aza-arenes to electron-deficient alkynes [4][5][6][7][8]. The reactive Huisgen 1,4-dipoles have been widely employed
  • unprecedented synthetic reactivity of the electron-deficient alkynes, but also provides efficient synthetic methodologies for complex nitrogen-containing heterocycles. The potential application of this reaction in organic synthesis and medicinal chemistry might be significant. Experimental General procedure for
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Published 29 Jun 2023

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

  • Haritha Sindhe,
  • Malladi Mounika Reddy,
  • Karthikeyan Rajkumar,
  • Akshay Kamble,
  • Amardeep Singh,
  • Anand Kumar and
  • Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

Graphical Abstract
  • Heck cross-coupling [69][70]. However, researchers have developed various methods for the transition-metal-catalyzed C(sp2)–H olefination using various types of alkenes as coupling partners [71][72][73]. This part of the review covers reports for the alkenylation of pyridine with terminal alkynes
  • , acrylates, allenes, and alkynes as coupling partners achieving the functionalized C(sp2)–H-olefinated pyridine frameworks via metal catalysis. ortho-C–H Alkenylation In 2012, Huang and co-workers [74] disclosed a ligand-free oxidative cross-coupling reaction of pyridine with acrylates, acrylamides, and
  • . Except lately, in 2020, Chen and group [82] reported a Pd/Cu-catalyzed regio- and stereoselective synthesis of C2-alkenylated pyridines starting from internal alkynes 84 and pyridinium salts in a stereodivergent manner (Scheme 17a). The interesting part of this work was the switching of the alkene
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Published 12 Jun 2023

Construction of hexabenzocoronene-based chiral nanographenes

  • Ranran Li,
  • Di Wang,
  • Shengtao Li and
  • Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

Graphical Abstract
  • -workers reported pyrrole-containing helical NGs 19 and 20. The precursors 17 and 18 were synthesized from pyrrole-containing alkynes and tetracyclone 2 through a typical Diels–Alder reaction. The pair of enantiomers of these aza-[5]helicenes was confirmed by the X-ray crystal structure of racemic
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Published 30 May 2023

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

  • Semyon V. Tsybulin,
  • Ekaterina A. Filatova,
  • Alexander F. Pozharskii,
  • Valery A. Ozeryanskii and
  • Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

Graphical Abstract
  • compounds 7a–e in 42–62% yields, but also gave higher amounts of products 9a–e (10–30%). Thus, the Pd- and phosphine-free Castro–Stephens coupling was a good enough alternative to synthesize alkynes 7. The structure of the double alkynylation product 9e was confirmed by X-ray diffraction data (see
  • recrystallization of the crude product from ethanol. Next, the oxidative dimerization of terminal alkynes 6a–e was carried out in an aerobic medium in the CuI/TMEDA/iPr2NH system at room temperature, which proved to be effective in the synthesis of butadiynes 1–4 [15] (Scheme 3). The desired diarylbutadiynes 5a–e
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Published 15 May 2023

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

Graphical Abstract
  • -alkynylketones 129 in good yields. Conjugate additions with organozirconium reagents The hydrozirconation of alkenes and alkynes generates mild organozirconium compounds that can be used in various transformations. Fletcher and co-workers developed the utilization of organozirconium reagents in Cu-catalyzed
  • derivatization is possible through the oxidation of the silyl motif to alcohol or the dehydration of the aldol adduct. Other tandem conjugate addition/enolate-trapping reactions In 2016, Nishiyama and co-workers have studied a three-component coupling reaction of alkynes, enones, and aldehydes via direct
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Published 04 May 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

Graphical Abstract
  • difunctionalization of norbornene derivatives 15 with alkynes (Scheme 3) [35]. It was noted the reaction is amenable to both electron-donating groups (EDGs) and electron-withdrawing groups (EWGs); however, yields were diminished with increasing electron deficiency. Moreover, the use of the bulkier tert
  • product 19c, the latter was obtained in a greatly reduced yield, perhaps due to less ring strain providing a thermodynamic driving force. In 2013, Mannathan et al. discussed a Ni-catalyzed intermolecular three-component difunctionalization of oxabicyclic alkenes 1 with organoboronic acids 20 and alkynes
  • exo face of 30b, oxidative cyclization can afford the ruthenacycle 101. Unlike previous works studying Ru-catalyzed cyclizations involving bicyclic alkenes and alkynes [56][57][58][59], the reaction preferentially undergoes β-hydride elimination to generate 102 rather than reductive elimination which
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Published 24 Apr 2023

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K3PO4

  • Ina Remy-Speckmann,
  • Birte M. Zimmermann,
  • Mahadeb Gorai,
  • Martin Lerch and
  • Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

Graphical Abstract
  • the standard reactions for catalytic hydrogenations with copper(I)/NHC complexes [4]. In this vein, we tested complex 5 from solid and liquid phase synthesis in the catalytic hydrogenation of esters, carbonyl compounds and in the semihydrogenation of alkynes. In the catalytic hydrogenation of ethyl
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Published 14 Apr 2023
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