Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Resonance Destabilization in N-Acylanilines (Anilides): Electronically-Activated Planar Amides of Relevance in N–C(O) Cross-Coupling

Resonance Destabilization in N-Acylanilines (Anilides): Electronically-Activated Planar Amides of Relevance in N–C(O) Cross-Coupling
Roman Szostak, Michal Szostak, Guangrong Meng
Transition-metal-catalyzed activation of amide N–C(O) bonds proceeds via selective metal insertion into the carbon–nitrogen amide bond. Herein, we demonstrate that N-acylanilines (anilides), the first class of planar amides that have been shown to undergo selective amide N–C cross-coupling reactions, feature a significantly decreased barrier to rotation around the amide N–C(O) bond. Most significantly, we demonstrate that amide nN → π*C═O resonance in simple anilides can be varied by as much as 10 kcal/mol. The data have important implications for the design of N–C(O) amide cross-coupling reactions and control of the molecular conformation of anilides by resonance effects.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00971

DOI: 10.1021/acs.joc.7b00971

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