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
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
