Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond delta to the pyridine nitrogen

Naoto Chatani; Shuhei Yorimitsu; Taku Asaumi; Fumitoshi Kakiuchi; Shinji Murai

doi:10.1021/jo0259865

Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond delta to the pyridine nitrogen

J Org Chem. 2002 Oct 18;67(21):7557-60. doi: 10.1021/jo0259865.

Authors

Naoto Chatani¹, Shuhei Yorimitsu, Taku Asaumi, Fumitoshi Kakiuchi, Shinji Murai

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. chatani@chem.eng.osaka-u.ac.jp

PMID: 12375998
DOI: 10.1021/jo0259865

Abstract

The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru3(CO)12 results in direct carbonylation at a C-H bond delta to the pyridine sp2 nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.