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Ground-state distortion in N-acyl-tert-butyl-carbamates (Boc) and N-acyl-tosylamides (Ts) : twisted amides of relevance to amide N−C cross-coupling.
Autorzy
Rok wydania
2016
Czasopismo
Numer woluminu
81
Strony
8091-8094
DOI
10.1021/acs.joc.6b01560
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Amide N–C(O) bonds are generally unreactive in cross-coupling reactions employing low-valent transition metals due to nN → π*C═O resonance. Herein we demonstrate that N-acyl-tert-butyl-carbamates (Boc) and N-acyl-tosylamides (Ts), two classes of acyclic amides that have recently enabled the development of elusive amide bond N–C cross-coupling reactions with organometallic reagents, are intrinsically twisted around the N–C(O) axis. The data have important implications for the design of new amide cross-coupling reactions with the N–C(O) amide bond cleavage as a key step.
Adres publiczny
http://dx.doi.org/10.1021/acs.joc.6b01560
Strona internetowa wydawcy
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