Issue 40, 2019

Electrochemical C–H bond activation via cationic iridium hydride pincer complexes

Abstract

A C–H bond activation strategy based on electrochemical activation of a metal hydride is introduced. Electrochemical oxidation of (tBu4PCP)IrH4 (tBu4PCP is [1,3-(tBu2PCH2)-C6H3]) in the presence of pyridine derivatives generates cationic Ir hydride complexes of the type [(tBu4PCP)IrH(L)]+ (where L = pyridine, 2,6-lutidine, or 2-phenylpyridine). Facile deprotonation of [(tBu4PCP)IrH(2,6-lutidine)]+ with the phosphazene base tert-butylimino-tris(pyrrolidino)phosphorane, tBuP1(pyrr), results in selective C–H activation of 1,2-difluorobenzene (1,2-DFB) solvent to generate (tBu4PCP)Ir(H)(2,3-C6F2H3). The overall electrochemical C–H activation reaction proceeds at room temperature without need for chemical activation by a sacrificial alkene hydrogen acceptor. This rare example of undirected electrochemical C–H activation holds promise for the development of future catalytic processes.

Graphical abstract: Electrochemical C–H bond activation via cationic iridium hydride pincer complexes

Supplementary files

Article information

Article type
Edge Article
Submitted
21 6月 2019
Accepted
19 8月 2019
First published
20 8月 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 9326-9330

Electrochemical C–H bond activation via cationic iridium hydride pincer complexes

B. M. Lindley, A. G. Walden, A. M. Brasacchio, A. Casuras, N. Lease, C. Chen, A. S. Goldman and A. J. M. Miller, Chem. Sci., 2019, 10, 9326 DOI: 10.1039/C9SC03076J

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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