Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light.

Org Biomol Chem

Department of Chemistry, Indian Institute of Technology, New Delhi-110016, India.

Published: April 2020

A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines and imidazo[1,2-a]quinolines is reported in the presence of eosin Y and visible light. The ring opening occurs under ambient conditions through singlet oxygen insertion, bond cleavage and CO2 elimination, and produces N-(pyridin-2-yl) amides and N-(quinolin-2-yl) amides in high yields. The reaction shows good versatility, and does not require strong external oxidants and additives.

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http://dx.doi.org/10.1039/d0ob00563kDOI Listing

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