Base-assisted transmetalation enables gold-catalyzed oxidative Sonogashira coupling reaction

Autor: Lizhu Zhang, Wenchao Zhang, Dinghua Li, Rongjie Yang, Zhonghua Xia
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: iScience, Vol 27, Iss 1, Pp 108531- (2024)
Druh dokumentu: article
ISSN: 2589-0042
DOI: 10.1016/j.isci.2023.108531
Popis: Summary: The traditional transition metal catalyzed neutral C(sp)-C(sp2) cross-coupling reaction between a nucleophile and an electrophile is a key technique for the formation of carbon-carbon bonds. Herein, we present a general gold-catalyzed oxidative Sonogashira cross-coupling of arylboronic acids and terminal arylalkynes at room temperature with excellent functional-group tolerance and good chemoselectivity. Moreover, our mechanistic studies suggested a third pathway involving a base-assisted transmetalation between the gold(I) catalyst and aryl boronic acid might predominate in our reaction conditions, rather than the previously assumed oxidation of the gold(I) complex or deprotonation of alkynes.
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