Angewandte Chemie. International edition in English 2016-08-08

Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.

Jie Wang, Tian Qin, Tie-Gen Chen, Laurin Wimmer, Jacob T Edwards, Josep Cornella, Benjamin Vokits, Scott A Shaw, Phil S Baran

Index: Angew. Chem. Int. Ed. Engl. 55(33) , 9676-9, (2016)

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Abstract

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 (NiCl2 ⋅6 H2 O-$9.5 mol(-1) , Et3 N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.