Employing arynes for the generation of aryl anion equivalents and subsequent reaction with aldehydes

TitleEmploying arynes for the generation of aryl anion equivalents and subsequent reaction with aldehydes
Publication TypeJournal Article
Year of Publication2018
AuthorsGaykar, RN, Bhunia, A, Biju, AT
JournalJournal of Organic Chemistry
Volume83
Issue18
Pagination11333-11340
Date PublishedSEP
Type of ArticleArticle
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.

DOI10.1021/acs.joc.8b01549
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.805

Divison category: 
Organic Chemistry