Premium
Synthesis of Active Hexafluoroisopropyl Benzoates through a Hydrogen‐Bond‐Enabled Palladium(II)‐Catalyzed C−H Alkoxycarbonylation Reaction
Author(s) -
Wang Yang,
Gevorgyan Vladimir
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611757
Subject(s) - chemistry , catalysis , aryl , silanes , benzoates , palladium , functional group , selectivity , silylation , medicinal chemistry , organic chemistry , hydrogen , nitrogen atom , combinatorial chemistry , group (periodic table) , polymer , alkyl , silane
A Pd II ‐catalyzed ortho C−H alkoxycarbonylation reaction of aryl silanes toward active hexafluoroisopropyl (HFIP) benzoate esters has been developed. This efficient reaction features high selectivity and good functional‐group tolerance. Notably, given the general nature of the silyl‐tethered directing group, this method delivers products bearing two independently modifiable sites. NMR studies reveal the presence of hydrogen bonding between HFIP and a pyrimidine nitrogen atom of the directing group, and it is thought to be crucial for the success of this alkoxycarbonylation reaction.