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Inne
Resonance destabilization in N-acylanilines (anilides) : electronically-activated planar amides of relevance in N—C(O) cross-coupling.
Autorzy
Rok wydania
2017
Czasopismo
Numer woluminu
82
Strony
6373-6378
DOI
10.1021/acs.joc.7b00971
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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 Nacylanilines (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.
Adres publiczny
http://dx.doi.org/10.1021/acs.joc.7b00971
Strona internetowa wydawcy
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