Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 39, Pages 11801-11805Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604321
Keywords
biaryls; C-C coupling; C-H activation; electrochemistry; protecting groups
Categories
Funding
- DFG [Wa1278/14-1]
- Max Planck Graduate Center
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The oxidative cross-coupling of aromatic substrates without the necessity of leaving groups or catalysts is described. The selective formation of partially protected nonsymmetric 2,2'-biphenols via electroorganic synthesis was accomplished with a high yield of isolated product. Since electric current is employed as the terminal oxidant, the reaction is reagent-free; no reagent waste is generated as only electrons are involved. The reaction is conducted in an undivided cell, and is suitable for scale-up and inherently safe. The implementation of Osilyl-protected phenols in this transformation results in both significantly enhanced yields and higher selectivity for the desired nonsymmetric 2,2'-biphenols. The use of a bulky silyl group to block one hydroxyl moiety makes the final product less prone to oxidation. Furthermore, the partially silylprotected 2,2'-biphenols are versatile building blocks that usually require tedious or low-yielding synthetic pathways. Additionally, this strategy facilitates a large variety of new substrate combinations for oxidative cross-coupling reactions.
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