Harnessing Vinyl Acetate as an Acetylene Equivalent in Redox-Neutral Cp*Co(III)-Catalyzed C-H Activation/Annulation for the Synthesis of Isoquinolones and Pyridones

Tamanna Rana; Arijit Ghosh; Yogesh N Aher; Amit B Pawar

doi:10.1021/acsomega.3c02352

Harnessing Vinyl Acetate as an Acetylene Equivalent in Redox-Neutral Cp*Co(III)-Catalyzed C-H Activation/Annulation for the Synthesis of Isoquinolones and Pyridones

ACS Omega. 2023 Jul 5;8(28):25262-25271. doi: 10.1021/acsomega.3c02352. eCollection 2023 Jul 18.

Authors

Tamanna Rana¹, Arijit Ghosh¹, Yogesh N Aher¹, Amit B Pawar¹

Affiliation

¹ School of Chemical Sciences, Indian Institute of Technology Mandi, Mandi, Himachal Pradesh 175005, India.

Abstract

We have developed Cp*Co(III)-catalyzed redox-neutral synthesis of 3,4-unsubstituted isoquinoline 1(2H)-ones at ambient temperature using N-chloroamides as a starting material. The reaction utilizes vinyl acetate as an inexpensive and benign acetylene surrogate. The N-Cl bond of the N-chlorobenzamides plays the role of an internal oxidant and hence precludes the need for an external oxidant. The reaction works with a wide range of substrates having various functional groups and a substrate containing a heterocyclic ring. Notably, the reaction is extended to the N-chloroacrylamides in which vinylic C-H activation occurs to furnish the 2-pyridone derivatives. Preliminary mechanistic studies were also conducted to shed light on the mechanism of this reaction.