Regioselective introduction of heteroatoms at the C-8 position of quinoline N-oxides: remote C–H activation using N-oxide as a stepping stone

H Hwang, J Kim, J Jeong, S Chang

Index: Kang, Taek; Kim, Youngchan; Lee, Donggun; Wang, Zhen; Chang, Sukbok Journal of the American Chemical Society, 2014 , vol. 136, # 11 p. 4141 - 4144

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Citation Number: 111

Abstract

Reported herein is the metal-catalyzed regioselective C–H functionalization of quinoline N- oxides at the 8-position: direct iodination and amidation were developed using rhodium and iridium catalytic systems, respectively. Mechanistic study of the amidation revealed that the unique regioselectivity is achieved through the smooth formation of N-oxide-chelated iridacycle and that an acid additive plays a key role in the rate-determining ...