☆ 4.3 Article

EFFICIENT MICROWAVE METHOD FOR THE OXIDATIVE COUPLING OF PHENOLS

SYNTHETIC COMMUNICATIONS (2015)

Journal

SYNTHETIC COMMUNICATIONS

Volume 45, Issue 3, Pages 331-337

Publisher

TAYLOR & FRANCIS INC

DOI: 10.1080/00397911.2014.956370

Keywords

Biaryl diol; binaphthol; microwave chemistry; phenoxyl radical

Categories

Chemistry, Organic

Funding

National Science Foundation [1151933]
Rose Hills Foundation
Keck Foundation Summer Research Grant
Direct For Mathematical & Physical Scien
Division Of Chemistry [1151933] Funding Source: National Science Foundation

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Abstract

The tert-butyl peroxide-initiated, oxidative coupling of phenols can frequently promote reactions that otherwise perform poorly under alternative conditions. Despite this utility, peroxide coupling reactions employing conventional heat often require high-dilution conditions, multiple additions of oxidant, and long reflux times, while regularly affording only moderate product yields. We recently developed an optimized protocol for peroxide-promoted, oxidative coupling that employs microwave heat. Product yields up to 98% have been attained. The performance and scope of this method relative to other oxidative coupling methodologies will be discussed.

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