Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant

Jin Wang; Chiyu Wei; Xuming Li; Pengyi Zhao; Chuan Shan; Lukasz Wojtas; Hao Chen; Xiaodong Shi

doi:10.1002/chem.202000166

Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant

Jin Wang, Chiyu Wei, Xuming Li, Pengyi Zhao, Chuan Shan, Lukasz Wojtas, Hao Chen, Xiaodong Shi

Chemistry and Environmental Science

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

18 Scopus citations

Abstract

Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.

Original language	English (US)
Pages (from-to)	5946-5950
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	27
DOIs	https://doi.org/10.1002/chem.202000166
State	Published - May 12 2020

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Keywords

alkyne
allene
diselenation
gold redox catalysis
mild oxidant

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10.1002/chem.202000166

Cite this

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title = "Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant",

abstract = "Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.",

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author = "Jin Wang and Chiyu Wei and Xuming Li and Pengyi Zhao and Chuan Shan and Lukasz Wojtas and Hao Chen and Xiaodong Shi",

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T1 - Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant

AU - Wang, Jin

AU - Wei, Chiyu

AU - Li, Xuming

AU - Zhao, Pengyi

AU - Shan, Chuan

AU - Wojtas, Lukasz

AU - Chen, Hao

AU - Shi, Xiaodong

PY - 2020/5/12

Y1 - 2020/5/12

N2 - Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.

AB - Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.

KW - alkyne

KW - allene

KW - diselenation

KW - gold redox catalysis

KW - mild oxidant

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 27

ER -

Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant

Abstract

All Science Journal Classification (ASJC) codes

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