期刊
ORGANIC LETTERS
卷 18, 期 17, 页码 4194-4197出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01836
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资金
- Rutgers University
- NSF-MRI Grant [CHE-1229030]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
- Priority Academic Program Development of Jiangsu Higher Education-Yangzhou University
- National Natural Science Foundation of China [21472616]
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 acylmetal 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.
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