title: Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds.
abstract: We herein report the palladium(II)-catalyzed bromination and iodination of a variety of α-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp3)-H bromination, enabled by quinoline ligands.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ru-Yi
authors.initials: RY
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Tyler G
authors.initials: TG
authors.lastname: Saint-Denis
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ying
authors.initials: Y
authors.lastname: Shao
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jian
authors.identifier: 0000-0002-3388-3239
authors.initials: J
authors.lastname: He
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Joshua D
authors.initials: JD
authors.lastname: Sieber
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jin-Quan
authors.identifier: 0000-0003-3560-5774
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D006842:Hydrocarbons, Brominated; D006847:Hydrocarbons, Iodinated; D008024:Ligands; D011804:Quinolines; D010165:Palladium; D006859:Hydrogen