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Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant
Author(s) -
Wang Jin,
Zhang Shuyao,
Xu Chang,
Wojtas Lukasz,
Akhmedov Novruz G.,
Chen Hao,
Shi Xiaodong
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201802540
Subject(s) - chemistry , catalysis , sulfonium , redox , alkyne , stereoselectivity , intramolecular force , combinatorial chemistry , substrate (aquarium) , photochemistry , organic chemistry , salt (chemistry) , oceanography , geology
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.