Premium
Transition‐Metal‐Free Activation of Amides by N−C Bond Cleavage
Author(s) -
Li Guangchen,
Szostak Michal
Publication year - 2020
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201900072
Subject(s) - amide , chemistry , peptide bond , bond cleavage , transition metal , nucleophile , combinatorial chemistry , organic synthesis , cleavage (geology) , inert , stereochemistry , organic chemistry , catalysis , materials science , fracture (geology) , composite material , enzyme
The amide bond N−C activation represents a powerful strategy in organic synthesis to functionalize the historically inert amide linkage. This personal account highlights recent remarkable advances in transition‐metal‐free activation of amides by N−C bond cleavage, focusing on both (1) mechanistic aspects of ground‐state‐destabilization of the amide bond enabling formation of tetrahedral intermediates directly from amides with unprecedented selectivity, and (2) synthetic utility of the developed transformations. Direct nucleophilic addition to amides enables a myriad of powerful methods for the formation of C−C, C−N, C−O and C−S bonds, providing a straightforward and more synthetically useful alternative to acyl‐metals.