Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex

Yong Yang, Robert M. Rioux

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

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

Original languageEnglish (US)
Pages (from-to)3916-3925
Number of pages10
JournalGreen Chemistry
Volume16
Issue number8
DOIs
StatePublished - Aug 2014

Fingerprint

Alkynes
alkene
thiol
Alkenes
Sulfhydryl Compounds
Olefins
catalyst
Stereoselectivity
electron
Catalysts
Electrons
Sulfides
Silicon Dioxide
Isomers
silica
Silica
sulfide
cost
Costs
SBA-15

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

Cite this

@article{0539ea14d5324606b01b67d3ef18d21f,
title = "Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex",
abstract = "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",
author = "Yong Yang and Rioux, {Robert M.}",
year = "2014",
month = "8",
doi = "10.1039/c4gc00642a",
language = "English (US)",
volume = "16",
pages = "3916--3925",
journal = "Green Chemistry",
issn = "1463-9262",
publisher = "Royal Society of Chemistry",
number = "8",

}

Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex. / Yang, Yong; Rioux, Robert M.

In: Green Chemistry, Vol. 16, No. 8, 08.2014, p. 3916-3925.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex

AU - Yang, Yong

AU - Rioux, Robert M.

PY - 2014/8

Y1 - 2014/8

N2 - 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

AB - 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

UR - http://www.scopus.com/inward/record.url?scp=84904895636&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84904895636&partnerID=8YFLogxK

U2 - 10.1039/c4gc00642a

DO - 10.1039/c4gc00642a

M3 - Article

AN - SCOPUS:84904895636

VL - 16

SP - 3916

EP - 3925

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 8

ER -