- Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.
Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.
Angewandte Chemie (International ed. in English) (2016-07-07)
Jie Wang, Tian Qin, Tie-Gen Chen, Laurin Wimmer, Jacob T Edwards, Josep Cornella, Benjamin Vokits, Scott A Shaw, Phil S Baran
PMID27380912
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.
MATERIALS