Carbonylation of C-N Bonds in Tertiary Amines Catalyzed by Low Valent Iron Catalysts

Tawfiq Nasr Allah (1) , Solène Savourey (1) , Jean-Claude Berthet (1) , Emmanuel Nicolas (1) , Thibault Cantat (1)

1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

The first iron catalysts able to promote the formal insertion of CO into the C-N bond of amines are reported. Using low valent iron complexes, including K2[Fe(CO)4], amides are formed from aromatic and aliphatic amines, in the presence of an iodoalkane promoter. Inorganic Lewis acids, such as AlCl3 and Nd(OTf)3, have a positive influence on the catalytic activity of the iron salts, enabling the carbonylation at a low pressure of CO (6 to 8 bars).

Keywords: Carbon Monoxide; Iron; Catalysis; Lewis Acids; Amides

Domains: Organic chemistry; Catalysis

Tawfiq Nasr Allah, Solène Savourey, Jean-Claude Berthet, Emmanuel Nicolas, Thibault Cantat. Carbonylation of C-N Bonds in Tertiary Amines Catalyzed by Low Valent Iron Catalysts. Angewandte Chemie International Edition, 2019, 58, pp.10884-10887. ⟨10.1002/anie.201903740⟩. ⟨cea-02145076⟩