Issue 95, 2021

Intermediates and mechanism in iron-catalyzed C–H methylation with trimethylaluminum

Abstract

A mechanistic study is performed on the reaction method for iron-catalyzed C–H methylation with AlMe3 reagent, previously proposed to involve cyclometalated iron(III) intermediates and an iron(III)/(I) reaction cycle. Detailed spectroscopic studies (57Fe Mössbauer, EPR) during catalysis and in stoichiometric reactions identify iron(II) complexes, including cyclometalated iron(II) intermediates, as the major iron species formed in situ under catalytic reaction conditions. Reaction studies identify a cyclometalated iron(II)-methyl species as the key intermediate leading to C–H methylated product upon reaction with oxidant, consistent with a previously proposed iron(II)/iron(III)/iron(I) reaction manifold for C–H arylation.

Graphical abstract: Intermediates and mechanism in iron-catalyzed C–H methylation with trimethylaluminum

Supplementary files

Article information

Article type
Communication
Submitted
04 ต.ค. 2564
Accepted
29 ต.ค. 2564
First published
16 พ.ย. 2564

Chem. Commun., 2021,57, 12784-12787

Author version available

Intermediates and mechanism in iron-catalyzed C–H methylation with trimethylaluminum

S. Bhatia, J. C. DeMuth and M. L. Neidig, Chem. Commun., 2021, 57, 12784 DOI: 10.1039/D1CC05607G

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