Gold-Catalyzed Hydroarylation of N‑Aryl Alkynamides for the Synthesis of 2‑Quinolinones

A mild method for the synthesis of 2-quinolinones via hydroarylation of N-aryl alkynamides is reported. While traditional methods have relied on the use of strong Brønsted or Lewis acids, this report describes the development of mild reaction conditions that yield 2-quinolinones in good to excellent...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-03, Vol.82 (5), p.2558-2569
Main Authors: Vacala, Taylor, Bejcek, Lauren P, Williams, Chloé G, Williamson, Alexandra C, Vadola, Paul A
Format: Article
Language:English
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Summary:A mild method for the synthesis of 2-quinolinones via hydroarylation of N-aryl alkynamides is reported. While traditional methods have relied on the use of strong Brønsted or Lewis acids, this report describes the development of mild reaction conditions that yield 2-quinolinones in good to excellent yield using a commercially available gold catalyst. Substrates bearing a variety of functional groups are presented, with N-substitution proving to be key to the reactivity of several substrates.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02984