title: Palladium catalyzed acetoxylation of benzylic C-H bonds using a bidentate picolinamide directing group.
abstract: A general palladium catalyzed acetoxylation of benzylic C-H bonds has been developed. Picolinamides serve as an excellent directing group for the C-H activation of benzylic methyls. A wide range of 2-amino benzyl alcohol analogues were synthesized in good yields. The products demonstrated broad synthetic utilities toward various benzo-fused heterocycles. Mechanistic studies revealed the key rate-limiting C-H insertion step, which could be affected by the substitution pattern of the parent arene.
authors.affiliation: Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China. huangyong@pkusz.edu.cn.
authors.forename: Tao
authors.initials: T
authors.lastname: Cheng
authors.forename: Weiyu
authors.initials: W
authors.lastname: Yin
authors.forename: Yi
authors.initials: Y
authors.lastname: Zhang
authors.forename: Yingnan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Yong
authors.initials: Y
authors.lastname: Huang
mesh_terms: D000577:Amides / Q000737:chemistry; D001592:Benzyl Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010848:Picolinic Acids / Q000737:chemistry*
chemical_list: D000577:Amides; D001592:Benzyl Alcohols; D001593:Benzyl Compounds; D009942:Organometallic Compounds; D010848:Picolinic Acids; C072332:2-aminobenzyl alcohol; D010165:Palladium; C003142:picolinamide