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. 2013 Apr 5;78(7):3030-8.
doi: 10.1021/jo400017v. Epub 2013 Feb 20.

Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system

Lehao Huang  1 , Qian Li, Chen Wang, Chenze Qi
Affiliations

Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system

Lehao Huang et al. J Org Chem. .

Abstract

A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.

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