Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes

被引：105

作者：

Ananikov, VP

Malyshev, DA

Beletskaya, IP

Aleksandrov, GG

Eremenko, IL

机构：

[1] Russian Acad Sci, Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] Lomonosov Moscow State Univ, Dept Chem, Moscow 119899, Russia

[3] Russian Acad Sci, Kurnakov Inst Gen & Inorgan Chem, Moscow 117907, Russia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 15期

关键词：

alkynes; catalytic reaction; nickel; regioselectivity; gamma-terpinene; vinyl sulphides;

D O I：

10.1002/adsc.200505168

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Regioselective Markovnikov-type addition of PhSH to alkynes (HC C-R) has been performed using easily available nickel complexes. The non-catalytic side reaction leading to anti-Markovnikov products was suppressed by addition of gamma-terpinene to the catalytic system. The other side reaction leading to the bis(phenylthio)alkene was avoided by excluding phosphine and phosphite ligands from the catalytic system. It was found that catalytic amounts of Et3N significantly increased the yield and selectivity of the catalytic reaction. Under optimized conditions high product yields of 60-85% were obtained for various alkynes [R=n-C5H11, CH2NMe2, CH2OMe, CH2SPh, C6H11 (OH), (CH2)(3)CN]. The X-ray structure of one of the synthesized products is reported.

引用

页码：1993 / 2001

页数：9

共 31 条

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