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H/D exchange under mild conditions in arenes and unactivated alkanes with C6D6 and D2O using rigid, electron-rich iridium PCP pincer complexes

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Abstract

The synthesis and characterization of an iridium polyhydride complex (Ir-H4) supported by an electron-rich PCP framework is described. This complex readily loses molecular hydrogen allowing for rapid room temperature hydrogen isotope exchange (HIE) at the hydridic positions and the α-C–H site of the ligand with deuterated solvents such as benzene-d6, toluene-d8 and THF-d8. The removal of 1–2 equivalents of molecular H2 forms unsaturated iridium carbene trihydride (Ir-H3) or monohydride (Ir-H) compounds that are able to create further unsaturation by reversibly transferring a hydride to the ligand carbene carbon. These species are highly active hydrogen isotope exchange (HIE) catalysts using C6D6 or D2O as deuterium sources for the deuteration of a variety of substrates. By modifying conditions to influence the Ir-Hn speciation, deuteration levels can range from near exhaustive to selective only for sterically accessible sites. Preparative level deuterations of select substrates were performed allowing for procurement of >95% deuterated compounds in excellent isolated yields; the catalyst can be regenerated by treatment of residues with H2 and is still active for further reactions.

Graphical abstract: H/D exchange under mild conditions in arenes and unactivated alkanes with C6D6 and D2O using rigid, electron-rich iridium PCP pincer complexes

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Article information


Submitted
11 May 2020
Accepted
15 Jun 2020
First published
16 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

H/D exchange under mild conditions in arenes and unactivated alkanes with C6D6 and D2O using rigid, electron-rich iridium PCP pincer complexes

J. D. Smith, G. Durrant, D. H. Ess, B. S. Gelfand and W. E. Piers, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02694H

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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    [Original citation] - Published by The Royal Society of Chemistry.

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