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The Superbase-Mediated Pairwise Substitution of the 2,2′- and 6,6′-Positions in a Biphenyl Derivative

✍ Scribed by Manfred Schlosser; Guiseppe Mangano; Frédéric Leroux

Book ID: 102171723
Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 112 KB
Volume: 2004
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300630

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✦ Synopsis

Abstract

The superbasic mixture of butyllithium and potassium tert‐butoxide is powerful enough to enable the double proton abstraction from one ortho and one ortho′ position of 4,4′‐di‐tert‐butylbiphenyl. In this way, a series of functionalized derivatives becomes readily accessible, among them 4,4′‐di‐tert‐butylbiphenyldiyl‐2,2′‐dicarboxylic acid (2a) and 4,4′‐di‐tert‐butylbiphenyl‐2,2′‐diol (2d). The latter compound can be subjected again to a superbase‐promoted double metalation, thus giving rise to 2,2′,6,6′‐tetrasubstituted biphenyl derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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