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N-acylsaccharins: stable electrophilic amide-based acyl transfer reagents in Pd-catalyzed Suzuki-Miyaura coupling via N—C cleavage.
Autorzy
Rok wydania
2016
Czasopismo
Numer woluminu
18
Strony
4194-4197
DOI
10.1021/acs.orglett.6b01836
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The development of efficient catalytic methods for N–C bond cleavage in amides remains an important synthetic challenge. The first Pd-catalyzed Suzuki–Miyaura cross-coupling of N-acylsaccharins with boronic acids by selective N–C bond activation is reported. The reaction enables preparation of a variety of functionalized diaryl and alkyl-aryl ketones with broad functional group tolerance and in good to excellent yields. Of general interest, N-acylsaccharins serve as new, highly reactive, bench-stable, economical, amide-based, electrophilic acyl transfer reagents via acyl-metal intermediates. Mechanistic studies strongly support the amide N–C(O) bond twist as the enabling feature of N-acylsaccharins in the N–C bond cleavage.
Adres publiczny
http://dx.doi.org/10.1021/acs.orglett.6b01836
Strona internetowa wydawcy
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