20025-27-8Relevant academic research and scientific papers
On the mechanism of n-butyl vinyl sulfide formation with [K(18-crown-6)SBu] as catalyst
Steinborn, Dirk,Rosenstock, Thomas,Sieler, Joachim
, p. 264 - 269 (1996)
n-Butyl mercaptane reacts with acetylene in the presence of [K(18-cr-6)SBu] as catalyst to give n-butyl vinyl sulfide. In toluene the reaction is of zeroth order with respect to BuSH and first order with respect to [K(18-cr-6)SBu]. The reaction
Potassium tert -Butoxide Mediated Reductive C-P Cross-Coupling of Arylvinyl Sulfides through C-S Bond Cleavage
Feng, Jie,Zhang, Qiaoling,Li, Fuhai,Yang, Lu,Kuchukulla, Ratnakar Reddy,Zeng, Qingle
supporting information, p. 224 - 228 (2020/10/30)
A transition-metal-free t -BuOK-mediated reductive C-P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C-S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C-P bond through C-S bond cleavage and reduction of a C-C double bond in one pot.
Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base
Zhao, Na,Lin, Chengdong,Wen, Lirong,Li, Zhibo
, p. 3432 - 3440 (2019/05/15)
Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed gre
N-heterocyclic carbene-catalyzed regio- and stereoselective hydrothiolation reaction of alkynes
Cong, Zi-Song,Zhang, Yang,Du, Guang-Fen,Gu, Cheng-Zhi,He, Lin
supporting information, p. 1838 - 1846 (2018/06/25)
N-heterocyclic carbenes (NHCs) have been utilized as Br?nsted base to catalyze the hydrothiolation reaction between alkynes and thiols to produce the vinyl sulfides stereoselectively.
Design of highly selective alkyne hydrothiolation RhI-NHC catalysts: Carbonyl-triggered nonoxidative mechanism
Palacios, Laura,Meheut, Yoann,Galiana-Cameo, María,Artigas, María José,DI Giuseppe, Andrea,Lahoz, Fernando J.,Polo, Victor,Castarlenas, Ricardo,Pérez-Torrente, Jesús J.,Oro, Luis A.
, p. 2198 - 2207 (2017/06/19)
New RhI-IPr (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-carbene) complexes bearing an N,O-pyridine-2-methanolato (N-O) bidentate ligand have been prepared. The carbonyl complex Rh(N-O)(IPr)(CO) efficiently catalyzes the hydrothiolation of
One-pot synthesis of alkyl styryl sulfides free from transition metal/ligand catalyst and thiols
Heredia, Adrian A.,Penenory, Alicia B.
, p. 991 - 997 (2013/03/14)
A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols. Copyright
Hydroxo-rhodium-N-heterocyclic carbene complexes as efficient catalyst precursors for alkyne hydrothiolation
Palacios, Laura,Artigas, Maria Jose,Polo, Victor,Lahoz, Fernando J.,Castarlenas, Ricardo,Perez-Torrente, Jesus J.,Oro, Luis A.
, p. 2910 - 2919 (2014/01/06)
The new Rh-hydroxo dinuclear complexes stabilized by an N-heterocyclic carbene (NHC) ligand of type [Rh(μ-OH)(NHC)(η2-olefin)] 2 (coe, IPr (3), IMes (4); ethylene, IPr (5)) are efficient catalyst precursors for alkyne hydrothiolation
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.
Lanthanum-catalyzed stereoselective synthesis of vinyl sulfides and selenides
Reddy, V. Prakash,Swapna,Kumar, A. Vijay,Rao, K. Rama
experimental part, p. 293 - 296 (2010/03/26)
Lanthanum oxide/TMEDA-catalyzed cross-coupling of vinyl halides with thiols/diphenyl diselenide in anhydrous DMSO and KOH is reported. Utilizing this protocol various vinyl sulfides and selenides were synthesized in excellent yields with retention of the stereochemistry. The catalyst was recyclable.
