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Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes

Author:
Gaykar, Rahul N., Bhunia, Anup, Biju, Akkattu T.
Source:
Journal of organic chemistry 2018 v.83 no.18 pp. 11333-11340
ISSN:
1520-6904
Subject:
Lewis acids, alcohols, aldehydes, anions, arylation, carbonates, chemical bonding, chemical structure
Abstract:
Arynes are highly reactive intermediates, which are utilized for the electrophilic arylation of various X–H bonds (X = O, N, S etc.). Herein, a new synthetic strategy is demonstrated, where arynes are converted into aryl anion equivalents by treatment with phosphines and a base. The addition of phosphines to arynes form the phosphonium salts, which in the presence of a carbonate base generates the aryl anion equivalent. Subsequent addition of the aryl anions with aldehydes afforded the secondary alcohols.
Agid:
6146176