title: 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.
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Jie
authors.initials: J
authors.lastname: Wang
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Tian
authors.initials: T
authors.lastname: Qin
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Tie-Gen
authors.initials: TG
authors.lastname: Chen
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Laurin
authors.initials: L
authors.lastname: Wimmer
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Jacob T
authors.initials: JT
authors.lastname: Edwards
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Josep
authors.initials: J
authors.lastname: Cornella
authors.affiliation: Discovery Chemistry, Bristol-Myers Squibb, 350 Carter Road, Hopewell, NJ, 08540, USA.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Vokits
authors.affiliation: Discovery Chemistry, Bristol-Myers Squibb, 350 Carter Road, Hopewell, NJ, 08540, USA.
authors.forename: Scott A
authors.initials: SA
authors.lastname: Shaw
authors.affiliation: The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA. pbaran@scripps.edu.
authors.forename: Phil S
authors.identifier: 0000-0001-9193-9053
authors.initials: PS
authors.lastname: Baran
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D001897:Boronic Acids; D004952:Esters; D009532:Nickel
keywords: Suzuki cross-coupling; decarboxylation; homogeneous catalysis; nickel catalysts; redox-active esters