Title

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

Document Type

Article

Publication Date

6-2018

Keywords

alkynes, gold redox catalysis, sulfonium cations, thioallylation, vinyl gold intermediates

Digital Object Identifier (DOI)

https://doi.org/10.1002/anie.201802540

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.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Angewandte Chemie International Edition English, v. 57, issue 23, p. 6915-6920

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