Regioselective Arylation of Amidoaryne Precursors via Ag‐Mediated Intramolecular Oxy‐Argentation

Autor:	Yong‐Ju Kwon, Ye‐Jin Kong, Min‐Jung Lee, Eun‐Hye Lim, Jaesung Kwak, Won‐Suk Kim
Jazyk:	angličtina
Rok vydání:	2024
Předmět:	amidobenzyne precursors aryne bimetallic cross‐coupling oxy‐argentation regioselective arylation Science
Zdroj:	Advanced Science, Vol 11, Iss 17, Pp n/a-n/a (2024)
Druh dokumentu:	article
ISSN:	2198-3844
DOI:	10.1002/advs.202308829
Popis:	Abstract An unprecedented silver‐mediated intramolecular oxy‐argentation of 3‐amidoaryne precursors that quickly generates a heteroarylsilver species is developed. AgF acts as both a stoichiometric fluoride source and a reagent for the formation of a benzoxazolylsilver intermediate via aryne generation. Pd‐catalyzed coupling reactions of (hetero)aryl iodides with a silver species, generated in situ, allow for the synthesis of various C7‐arylated benzoxazoles. As a result, an aryl group is selectively introduced into the meta‐position of 3‐amidobenzyne precursors. Mechanistic studies have indicated the presence of a benzoxazolylsilver intermediate and revealed that the reaction proceeds via an intramolecular oxy‐argentation process, which is initiated by a direct fluoride attack on the silyl group.
Databáze:	Directory of Open Access Journals
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