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

Gaykar, Rahul N. ; Bhunia, Anup ; Biju, Akkattu T. (2018) Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes The Journal of Organic Chemistry, 83 (18). pp. 11333-11340. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.8b01549

Related URL: http://dx.doi.org/10.1021/acs.joc.8b01549

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128625
Deposited On:03 Nov 2022 06:49
Last Modified:03 Nov 2022 06:49

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