Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols

Siti Nurhanna Riduan; Jackie Y. Ying; Yugen Zhang

doi:10.1021/ol3003699

Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols

Siti Nurhanna Riduan
, Jackie Y. Ying^*
, Yugen Zhang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

87 Scopus citations

Abstract

A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO ₂ atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO ₂ 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.

Original language	English
Pages (from-to)	1780-1783
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	7
DOIs	https://doi.org/10.1021/ol3003699
State	Published - 6 Apr 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3003699

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title = "Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols",

abstract = "A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO 2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO 2 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.",

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AU - Nurhanna Riduan, Siti

AU - Ying, Jackie Y.

AU - Zhang, Yugen

PY - 2012/4/6

Y1 - 2012/4/6

N2 - A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO 2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO 2 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.

AB - A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO 2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO 2 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.

UR - https://www.scopus.com/pages/publications/84859609565

U2 - 10.1021/ol3003699

DO - 10.1021/ol3003699

M3 - Article

C2 - 22432835

AN - SCOPUS:84859609565

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JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols

Abstract

ASJC Scopus subject areas

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