Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride

Abstract

A new and efficient process for transferring NH4Cl to both linear and branched primary amides has been achieved via palladium-catalyzed hydroaminocarbonylation of alkenes.

Recent Advances in the Functionalization of Hydrocarbons: Synthesis of Amides and its Derivatives

“…In the same line, Huang and co‐workers developed a facile and efficient palladium‐catalyzed aminocarbonylation method for the synthesis of linear or branched primary amides from alkenes, NH 4 Cl as amine source, and carbon monoxide (Scheme ) . After screening the various ammonium salts, NH 4 Cl was found to be more efficient in this reaction.…”

Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene

“…They are ubiquitous in natural products, functional materials, marketed drugs, and pesticides [20][21][22][23], and are attractive intermediates for diverse synthesis [24,25]. Different from the traditional preparation of amides via condensation between carboxylic derivatives and amines, the aminocarbonylations of olefins with amines have been developed as amide synthesis routes over the last two decades [22][23][24][25][26][27][28][29][30][31][32][33][34]. However, the reductive carbonylation of olefins with nitroarenes to produce amides has rarely been investigated, although it could be a promising alternative with readily available nitroarenes as the N-resource and better step-economy.…”

Hydroaminocarbonylation of Alkynes to Produce Primary α,β‐Unsaturated Amides Using NH4HCO3 Dually as Ammonia Surrogate and Brønsted Acid Additive

“…Very recently, Huang and co‐workers developed an elegant palladium‐catalyzed hydroaminocarbonylation of alkenes with solid NH 4 Cl to synthesize the primary amides [Scheme , Eq. (1)] …”