Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade

We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki-Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.

Automated summary

This study presents a new method for adding two different nucleophiles to the carbonyl carbon of an amide in a single step, leading to the conversion of amides to chiral alcohols. The use of non-precious-metal catalysis enables this one-pot process, potentially allowing for the development of new transformations converting carboxylic acid derivatives to functional groups with stereogenic centers.