E-resources
Peer reviewed
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Liu, Chengwei; Meng, Guangrong; Liu, Yongmei; Liu, Ruzhang; Lalancette, Roger; Szostak, Roman; Szostak, Michal
Organic letters, 09/2016, Volume: 18, Issue: 17Journal Article
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.
