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 jun. 2019
Accepted
19 ago. 2019
First published
20 ago. 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

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