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

Yu-Chao Yuan (1) , Raghu Kamaraj (1) , Christian Bruneau (1) , Thierry Labasque (2) , Thierry Roisnel (1) , Rafael Gramage-Doria (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 GR - Géosciences Rennes

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Domains: Organic chemistry

Yu-Chao Yuan, Raghu Kamaraj, Christian Bruneau, Thierry Labasque, Thierry Roisnel, et al.. Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives. Organic Letters, 2017, 19 (23), pp.6404-6407. ⟨10.1021/acs.orglett.7b03278⟩. ⟨insu-01639565⟩