Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant

Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G. Akhmedov; Hao Chen; Xiaodong Shi

doi:10.1002/anie.201802540

Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant

Jin Wang, Shuyao Zhang, Chang Xu, Lukasz Wojtas, Novruz G. Akhmedov, Hao Chen, Xiaodong Shi

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

55 Scopus citations

Abstract

Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for Au^I/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.

Original language	English (US)
Pages (from-to)	6915-6920
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	23
DOIs	https://doi.org/10.1002/anie.201802540
State	Published - Jun 4 2018
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

alkynes
gold redox catalysis
sulfonium cations
thioallylation
vinyl gold intermediates

Access to Document

10.1002/anie.201802540

Cite this

@article{88a294a994754b1d915cd7616ef8c69f,

title = "Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant",

abstract = "Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 \% catalyst loading, up to 99 \% yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.",

keywords = "alkynes, gold redox catalysis, sulfonium cations, thioallylation, vinyl gold intermediates",

author = "Jin Wang and Shuyao Zhang and Chang Xu and Lukasz Wojtas and Akhmedov, \{Novruz G.\} and Hao Chen and Xiaodong Shi",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = jun,

day = "4",

doi = "10.1002/anie.201802540",

language = "English (US)",

volume = "57",

pages = "6915--6920",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "23",

}

TY - JOUR

T1 - Highly Efficient and Stereoselective Thioallylation of Alkynes

T2 - Possible Gold Redox Catalysis with No Need for a Strong Oxidant

AU - Wang, Jin

AU - Zhang, Shuyao

AU - Xu, Chang

AU - Wojtas, Lukasz

AU - Akhmedov, Novruz G.

AU - Chen, Hao

AU - Shi, Xiaodong

PY - 2018/6/4

Y1 - 2018/6/4

N2 - Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.

AB - Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.

KW - alkynes

KW - gold redox catalysis

KW - sulfonium cations

KW - thioallylation

KW - vinyl gold intermediates

UR - https://www.scopus.com/pages/publications/85046539969

UR - https://www.scopus.com/inward/citedby.url?scp=85046539969&partnerID=8YFLogxK

U2 - 10.1002/anie.201802540

DO - 10.1002/anie.201802540

M3 - Article

C2 - 29663659

AN - SCOPUS:85046539969

SN - 1433-7851

VL - 57

SP - 6915

EP - 6920

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 23

ER -

Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this