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Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
Author(s) -
Hu Long,
Dietl Martin C.,
Han Chunyu,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016595
Subject(s) - alkynylation , bimetallic strip , catalysis , chemistry , tandem , context (archaeology) , phenols , combinatorial chemistry , organic chemistry , materials science , paleontology , composite material , biology
The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C−H alkynylation of phenols and oxy‐alkynylation of the newly introduced triple bond by using a unique redox property and the carbophilic π acidity of gold. Mechanistic studies support the participation of a bimetallic gold–silver species. The one‐pot protocol offers a direct, simple, and regio‐specific approach to 3‐alkynyl benzofurans from readily available phenols. A broad range of substrates, including heterocycles, is transferred with excellent functional group tolerance. Thus, this methodology can be used for the late‐stage incorporation of benzofurans.