Direct Use of Phosphonium Salts for Alkylation of <i>p</i>-Quinols: Formal α-Arylation of Carbonyls via a 5-Membered Betaine-Type Intermediate

Abstract

Unlike phosphonium ylides used extensively for C═C bond formation, herein we disclose the direct use of phosphonium salts for site-selective alkylation to p-quinols via a 5-membered betaine-type intermediate. This strategy provides a novel and general approach for the synthesis of α-(m-aminoaryl) esters, amides and ketones under ambient conditions. The reaction proceeds through in situ generation of P-ylide, alkylation and aromatization. Reaction is highly compatible with diverse functional phosphonium salts and amines.

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