Preparation of Amides via Intermolecular Dehydrogenative Coupling of Alcohols with Amines

Key words

ruthenium catalysis - dehydrogenative coupling - pincer complex - Milstein catalyst

Significance

Miltstein and co-workers reported a direct catalytic approach for the preparation of amides from alcohols and amines. The reaction proceeds under mild conditions, with low catalyst loading (0.1 mol%), and affords the products in excellent yields. It offers an attractive, atom-economical alternative to conventional acylation of amines.

Comment

The reaction is sensitive to steric hindrance, as the presence of α-substituents on either the alcohol or amine led to reduced yields of the desired product, while secondary amines showed no reactivity. Notably, unreacted starting material alcohol is converted into its corresponding ester product.

Review

C. Gunanathan, D. Milstein Science 2013 , 341, 1229712.

Publication History

Article published online:
18 August 2020