Issue 14, 2018

Cobalt-catalyzed directed ortho-methylation of arenes with methyl tosylate

Abstract

A cobalt-catalyzed directed ortho C–H methylation reaction of arenes has been achieved using readily available methyl tosylate as a methylating agent. An in situ-generated cobalt–N-heterocyclic carbene catalyst in combination with neopentylmagnesium bromide promotes the methylation at room temperature. The reaction is applicable to various substrates bearing nitrogen directing groups such as N-aryl imine, N–H imine, and 2-pyridyl groups. The present protocol also allows for facile introduction of a trideuteriomethyl group into arenes.

Graphical abstract: Cobalt-catalyzed directed ortho-methylation of arenes with methyl tosylate

Supplementary files

Article information

Article type
Research Article
Submitted
01 May 2018
Accepted
12 Jun 2018
First published
13 Jun 2018

Org. Chem. Front., 2018,5, 2214-2218

Cobalt-catalyzed directed ortho-methylation of arenes with methyl tosylate

Q. Sun and N. Yoshikai, Org. Chem. Front., 2018, 5, 2214 DOI: 10.1039/C8QO00438B

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