7214-57-5Relevant academic research and scientific papers
A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations
Tidei, Caterina,Sancineto, Luca,Bagnoli, Luana,Battistelli, Benedetta,Marini, Francesca,Santi, Claudio
supporting information, p. 5968 - 5975 (2015/03/30)
Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste
Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex
Yang, Yong,Rioux, Robert M.
, p. 3916 - 3925 (2014/08/05)
A practical, efficient, and low-cost heterogeneous catalyst consisting of a Cu-NHC (N-heterocyclic carbene) complex grafted to SBA-15 silica for the catalytic hydrothiolation of alkynes and electron-deficient alkenes under mild reaction conditions has been developed. The heterogeneous catalyst displays higher activity and stereoselectivity to Z-anti-Markovnikov isomers compared with the homogeneous analog under otherwise identical reaction conditions. The catalytic system is applicable to a broad range of alkynes and thiols and is recyclable without significant loss in catalytic performance. High activity and perfect selectivity to alkyl sulfides formed by the addition of electron-deficient alkenes to various thiols catalyzed by the supported Cu-NHC complex were also realized. This journal is the Partner Organisations 2014.
Alkyne hydrothiolation catalyzed by a dichlorobis(aminophosphine) complex of palladium: Selective formation of cis-configured vinyl thioethers
Gerber, Roman,Frech, Christian M.
scheme or table, p. 8901 - 8905 (2012/09/25)
Cis all round: Dichlorobis[1-(dicyclohexylphosphanyl)piperidine]palladium, [(P{(NC5H10)(C6H11) 2})2Pd(Cl)2], is a highly efficient alkyne hydrothiolation catalyst and the first generally applicable system that selectively generates cis-configured anti-Markovnikov adducts in excellent yields within only a few minutes at 120 °C in the presence of only 0.05 mol % of the catalyst (see scheme).
Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols
Nurhanna Riduan, Siti,Ying, Jackie Y.,Zhang, Yugen
supporting information; experimental part, p. 1780 - 1783 (2012/06/04)
A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO2 atmosphere. The reaction system is robust and utilizes inexpensive, readily available substrates. A cyclic alkene/carboxylate copper complex intermediate is proposed as the key step in determining the stereoselectivity, and an equivalent amount of water is found to play an active role as a proton donor.
Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C-S cross-coupling
Ranjit, Sadananda,Duan, Zhongyu,Zhang, Pengfei,Liu, Xiaogang
supporting information; experimental part, p. 4134 - 4136 (2010/11/17)
A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of CuI and Cs2CO 3, a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.
