Ni-catalyzed Cross-coupling of Redox-Active Esters with Boronic Acids

A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, speci...

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Published inAngewandte Chemie International Edition Vol. 55; no. 33; pp. 9676 - 9679
Main Authors Wang, Jie, Qin, Tian, Chen, Tie-Gen, Wimmer, Laurin, Edwards, Jacob T., Cornella, Josep, Vokits, Benjamin, Shaw, Scott A., Baran, Phil S.
Format Journal Article
LanguageEnglish
Published 06.07.2016
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Summary:A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N -hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl 2 •6H 2 O – $9.5/mol, Et 3 N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption. A cross-coupling between alkyl carboxylic acids and aryl boronic acids is enabled by a new activation/cross-coupling strategy under Nickel catalysis. The operational simplicity and the wide range of heterocyclic compounds make a convenient strategy for obtaining aryl-alkyl cross-coupling products.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201605463