Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes

William J Kerr; Marc Reid; Tell Tuttle

doi:10.1002/anie.201702997

Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes

Angew Chem Int Ed Engl. 2017 Jun 26;56(27):7808-7812. doi: 10.1002/anie.201702997. Epub 2017 Jun 7.

Authors

William J Kerr¹, Marc Reid¹, Tell Tuttle¹

Affiliation

¹ Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, G1 1XL, UK.

PMID: 28510987
DOI: 10.1002/anie.201702997

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 method is also described. Computational studies support kinetic product control over competing aromatic labeling and decarbonylation pathways.

Keywords: C−H activation; DFT; aldehydes; deuteration; iridium.

Publication types

Research Support, Non-U.S. Gov't