TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines.
It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.
Huang
Chunhui
C
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Gevorgyan
Vladimir
V
D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D006842:Hydrocarbons, Brominated; D055601:Organic Chemistry Phenomena; D010165:Palladium; D010636:Phenols / Q000737:chemistry*
D000814:Aniline Compounds; D006842:Hydrocarbons, Brominated; D010636:Phenols; D010165:Palladium; C023650:aniline