Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling

Abstract

This Graphical Review provides an overview of amide bond activation achieved by selective oxidative addition of the N-C(O) acyl bond to transition metals and nucleophilic acyl addition, resulting in acyl and decarbonylative coupling together with key mechanistic details pertaining to amide bond distortion underlying this reactivity manifold.

Keywords: C–N activation; acyl addition; acyl coupling; amide bond activation; catalysis; decarbonylative coupling.

Figure 1

Amide bond activation: concept and discoveries.

Figure 2

Transition-metal-catalyzed acyl Suzuki-Miyaura coupling of amides.

Figure 3

Synthesis of ketone via transition-metal-catalysis and metal-fee conditions.

Figure 4

Amides as acylating reagents in various synthetic methodologies.

Figure 5

Cross-coupling of amides with versatile partners.

Figure 6

Transamidation of amides under metal-catalysis and metal-free conditions.

Figure 7

Esterification of amides via metal-catalysis and metal-free conditions.

Figure 8

Decarbonylative cross-coupling of amides: discoveries and mechanism.

Figure 9

Decarbonylative cross-coupling of amides: construction of carbon-carbon and carbon-hydrogen bonds.

Figure 10

Decarbonylative cross-coupling of amides: construction of carbon-heteroatom bonds.^,