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- Title
Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.
- Authors
Wang, Jie; Qin, Tian; Chen, Tie ‐ Gen; Wimmer, Laurin; Edwards, Jacob T.; Cornella, Josep; Vokits, Benjamin; Shaw, Scott A.; Baran, Phil S.
- 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 H2O-$9.5 mol−1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.
- Subjects
NICKEL catalysts; OXIDATION-reduction reaction; ESTERS; BORONIC acids; ALKYL compounds; CHEMICAL reactions
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 33, p9828
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201605463