Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

Yu-Chao Yuan, Raghu Kamaraj, Christian Bruneau, Thierry Labasque, Thierry Roisnel and Rafael Gramage-Doria*

*Organometallics: Materials and Catalysis Laboratory, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS, Université de Rennes 1, 35042 Rennes, France, Email: rafael.gramage-doriauniv-rennes1.fr

Y.-C. Yuan, R. Kamaraj, C. Brunaeu, T. Labasque, T. Roisnel, R. Gramage-Doria, Org. Lett., 2017, 19, 6404-6407.

DOI: 10.1021/acs.orglett.7b03278

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Abstract

A ruthenium catalyst enables an unprecedented transformation of a wide range of phthalimides into amides in high yields and short reaction time in a single-step. The mechanism involces a unique, homogeneous pathway via five-membered ring opening and CO₂ release with water as source of protons.

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proposed mechanism

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Key Words

phthalimides, cleavage of imides

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ID: J54-Y2017