Iridium-catalyzed formyl-selective deuteration of aldehydes

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Kerr, William J. and Reid, Marc and Tuttle, Tell (2017) Iridium-catalyzed formyl-selective deuteration of aldehydes. Angewandte Chemie International Edition, 56 (27). 7808–7812. ISSN 1521-3773 (https://doi.org/10.1002/anie.201702997)

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Abstract

We report the first direct catalytic method for formyl-selective deuterium labeling of aromatic aldehydes under mild conditions, using an iridium-based catalyst designed to favor formyl- over aromatic C-H activation. A good range of aromatic aldehydes is selectively labeled, and a one-pot labeling/olefination protocol is also described. Computational studies support kinetic product control over competing aromatic labeling and decarbonylation pathways.

ORCID iDs

Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Reid, Marc ORCID logoORCID: https://orcid.org/0000-0003-4394-3132 and Tuttle, Tell;
CORE (COnnecting REpositories)