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

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.

SUBMITTER: Wang J 

PROVIDER: S-EPMC5232357 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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

Wang Jie J   Qin Tian T   Chen Tie-Gen TG   Wimmer Laurin L   Edwards Jacob T JT   Cornella Josep J   Vokits Benjamin B   Shaw Scott A SA   Baran Phil S PS  

Angewandte Chemie (International ed. in English) 20160706 33

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 t  ...[more]

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