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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 ?-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.

SUBMITTER: Wang J

PROVIDER: S-EPMC6121218 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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

Wang Jin J Zhang Shuyao S Xu Chang C Wojtas Lukasz L Akhmedov Novruz G NG Chen Hao H Shi Xiaodong X

Angewandte Chemie (International ed. in English) 20180507 23

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<sup>I/III</sup> coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for g ...[more]

PMID: 29663659

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