Nickel‐Catalyzed Cross‐Coupling of Redox‐Active Esters with Boronic Acids |
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| Authors: | Dr Jie Wang Dr Tian Qin Dr Tie‐Gen Chen Dr Laurin Wimmer Jacob T Edwards Dr Josep Cornella Benjamin Vokits Dr Scott A Shaw Prof Phil S Baran |
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| Affiliation: | 1. The Scripps Research Institute (TSRI), La Jolla, CA, USA;2. Discovery Chemistry, Bristol-Myers Squibb, Hopewell, NJ, USA |
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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 H2O—$9.5 mol?1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption. |
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| Keywords: | decarboxylation homogeneous catalysis nickel catalysts redox-active esters Suzuki cross-coupling |
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