N-Acylsaccharins: Stable Electrophilic Amide-Based Acyl Transfer Reagents in Pd-Catalyzed Suzuki–Miyaura Coupling via N–C Cleavage

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• 作者：Chengwei Liu ; Guangrong Meng ; Yongmei Liu ; Ruzhang Liu ; Roger Lalancette ; Roman Szostak ; Michal Szostak
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4194-4197
• 全文大小：358K
• 年卷期：0
• ISSN：1523-7052

文摘

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.