Iridium-catalyzed formyl-selective deuteration of aldehydes

Kerr, William John and Reid, Marc and Tuttle, Tell (2017) Iridium-catalyzed formyl-selective deuteration of aldehydes. Angewandte Chemie International Edition, 56 (27). 7808–7812. ISSN 1433-7851

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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.