Issue 30, 2021

Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature

Abstract

An efficient synthesis of substituted 3,4-dihydroisoquinolinones through [4+2]-annulation of N-chlorobenzamides/acrylamides having a monodentate directing group with alkylidenecyclopropanes in the presence of a less expensive, highly abundant and air stable Co(III) catalyst via a C–H activation is demonstrated. In this reaction, the N–Cl bond of N-chlorobenzamide serves as an internal oxidant and thus an external metal oxidant is avoided. The 3,4-dihydroisoquinolinone derivatives are converted successfully into the highly useful imidoyl chloride derivatives. The deuterium labeling and kinetic isolabelling studies reveal that the C–H activation is a rate-determining step in this cyclization reaction.

Graphical abstract: Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature

Supplementary files

Article information

Article type
Communication
Submitted
04 Feb 2021
Accepted
09 Mar 2021
First published
09 Mar 2021

Chem. Commun., 2021,57, 3692-3695

Cobalt(III)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature

B. Ramesh and M. Jeganmohan, Chem. Commun., 2021, 57, 3692 DOI: 10.1039/D1CC00654A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements