Nickel‐Catalyzed Cross‐Coupling of Redox‐Active Esters with Boronic Acids. Issue 33 (6th July 2016)

• Record Type: Journal Article
• Authors: Wang, Jie; Qin, Tian; Chen, Tie‐Gen; Wimmer, Laurin; Edwards, Jacob T.; Cornella, Josep; Vokits, Benjamin; Shaw, Scott A.; Baran, Phil S.
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 33(2016)
• Page Start: 9676
• Page End: 9679
• Publication Date: 2016-07-06
• Subjects: decarboxylation -- homogeneous catalysis -- nickel catalysts -- redox-active esters -- Suzuki cross-coupling; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201605463
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : 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.