期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2017, 期 46, 页码 6840-6850出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701322
关键词
Fluorinated compounds; Fluorine; Ketones; Weinreb amides; Nucleophilic substitution; Tandem reaction
资金
- Thailand Research Fund [BRG5850012, IRN58W0005]
- Center of Excellence for Innovation in Chemistry (PERCH-CIC)
- Postgraduate Education Research Development Office
- Office of the Higher Education Commission
- Mahidol University under the National Research Universities Initiative
- Centre National de la Recherche Scientifique (CNRS)-Projet International de Cooperation Scientifique (PICS) [PICS 6663]
- The Franco-Thai Cooperation Program in Higher Education and Research (PHC-Siam)
- Institute for the Promotion of Teaching Science and Technology
- Science Achievement Scholarship of Thailand (SAST)
[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were converted into difluoromethyl ketones through selective reductive cleavage of the phenylsulfanyl group. The reaction of o-alkynyl Weinreb amides derived from benzoic acid derivatives resulted in the formation of cyclized products through a 5-exo-dig cyclization.
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