Metal- and reagent-free highly selective anodic cross-coupling reaction of phenols.

Angew Chem Int Ed Engl

Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz (Germany) http//www.chemie.uni-mainz.de/OC/AK-Waldvogel/

Published: May 2014

The direct oxidative cross-coupling of phenols is a very challenging transformation, as homo-coupling is usually strongly preferred. Electrochemical methods circumvent the use of oxidizing reagents or metal catalysts and are therefore highly attractive. Employing electrolytes with a high capacity for hydrogen bonding, such as methanol with formic acid or 1,1,1,3,3,3-hexafluoro-2-propanol, a direct electrolysis in an undivided cell provides mixed 2,2'-biphenols with high selectivity. This mild method tolerates a variety of moieties, for example, tert-butyl groups, which are not compatible with other strong electrophilic media but vital for later catalytic applications of the formed products.

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http://dx.doi.org/10.1002/anie.201400627DOI Listing

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