Issue 15, 2020

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

Abstract

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.

Graphical abstract: Singlet oxygen mediated dual C–C and C–N bond cleavage in visible light

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2020
Accepted
26 Mar 2020
First published
26 Mar 2020

Org. Biomol. Chem., 2020,18, 2921-2928

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

Ritu, C. Sharma, S. Kumar and N. Jain, Org. Biomol. Chem., 2020, 18, 2921 DOI: 10.1039/D0OB00563K

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