Cobalt(III)-Catalyzed Regio- and Chemoselective [4 + 2]-Annulation of N-Chlorobenzamides/Acrylamides with 1,3-Dienes at Room Temperature.

Balu Ramesh, Masilamani Jeganmohan

The Journal of organic chemistry 2022 May 06

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Co(III)-catalyzed regio- and chemoselective redox-neutral C-H annulation of arylamides/acrylamides with 1,3-dienes is described. The present annulation reaction was well suited with a less-reactive 1,3-butadiene. By employing this protocol, pharmaceutically important 3,4-dihydroisoquinolinones were synthesized in good yields. Furthermore, the prepared 3,4-dihydroisoquinolinones were converted into highly important oxirane derivatives in good yields. A plausible mechanistic cycle is proposed and supported by a competition experiment and kinetic isotopic effect (KIE) studies.

Citation

Balu Ramesh, Masilamani Jeganmohan. Cobalt(III)-Catalyzed Regio- and Chemoselective [4 + 2]-Annulation of N-Chlorobenzamides/Acrylamides with 1,3-Dienes at Room Temperature. The Journal of organic chemistry. 2022 May 06;87(9):5713-5729