One‐Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant

Abstract

Rh‐catalyzed one‐step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69–83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were obtained in 62–79 % yields.

Symmetrical Tertiary Amines: Applications and Synthetic Approaches

“…In 2019 Chusov and co‐authors developed a rhodium‐catalyzed procedure for the tertiary symmetrical amines preparation via the reductive amination of (NH 4 ) 2 CO 3 utilizing CO as a reducing agent. [ 176 ] (NH 4 ) 2 CO 3 is a cheap ammonia synthetic equivalent allowing the use of the stoichiometric amount of the nitrogen source. This reaction proceeds smoothly with meta ‐ and para ‐substituted electron‐donor and electron‐acceptor benzaldehydes, and with aliphatic aldehydes with the substituents at the α ‐position to the carbonyl group (Scheme 66).…”