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

Authors

Jin Wang, University of South Florida
Shuyao Zhang, University of South Florida
Lukasz Wojtas, University of South FloridaFollow
Xiaodong Shi, University of South FloridaFollow
Chang Xu, Ohio University
Hao Chen, Ohio University
Novruz G. Akhmedov, West Virginia University

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 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.

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

Scholar Commons Citation

Wang, Jin; Zhang, Shuyao; Wojtas, Lukasz; Shi, Xiaodong; Xu, Chang; Chen, Hao; and Akhmedov, Novruz G., "Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant" (2018). Chemistry Faculty Publications. 79.
https://digitalcommons.usf.edu/chm_facpub/79