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9.1 Oxidative Dimerization of Phenols

DOI: 10.1055/sos-SD-225-00304

Lumb, J.-P.; Esguerra, K. V. N.Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (20171589.

The oxidative dimerization of phenols is implicated in the biosynthesis of numerous natural products (Scheme 6).[‌41‌‌44‌] However, the factors that govern the controlled recombination of phenoxyl radicals in biosynthesis remain poorly understood, despite evidence for the involvement of non-redox-active dirigent proteins.[‌43‌‌45‌] These biosynthetic, dehydrogenative C—C or C—O coupling reactions differ from reactions catalyzed by organometallic complexes due to the absence of discrete metal–substrate interactions in the bond-forming event.[‌46‌] Biosynthetic couplings do not rely on directing-group strategies or necessitate prefunctionalized starting materials, but instead rely on careful positioning of two radical intermediates within the confines of a dirigent proteinʼs active site to ensure high levels of regio- and stereocontrol. In the absence of these enzymes, oxidative coupling of phenols with electronically and sterically comparable ortho- and/or para-positions results in complex product mixtures.

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