RhI-catalyzed site-selective decarbonylative alkenylation and arylation of quinolones under chelation assistance

Abstract

An efficient catalytic system for the C-2 selective C-H functionalization of 4-quinolones was developed by using a decarbonylative coupling strategy. The installation of an N-pyrimidyl group on the quinolone nitrogen atom redirected the coordination between the catalyst and the carbonyl group to promote direct C-H functionalization at the 2-position of 4-quinolones. In addition, the present protocol was successfully applied to the C-3 selective installation of a variety of aryl and vinyl groups on an isoquinolone scaffold. The C-2 selective alkenylation and arylation reactions of 4-quinolones were achieved by using a RhI-catalyzed decarbonylative coupling strategy to afford valuable C-2 functionalized 4-quinolones. The present method was compatible with a broad scope of substrates and applied to the C-3 selective functionalization of an isoquinolone scaffold. Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim