期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 12, 页码 2706-2717出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500010
关键词
Synthetic methods; Chemoselectivity; Alcohols; Azides; Amides; Copper
资金
- Indian Institute of Science (IISc)
- Council of Scientific and Industrial Research (CSIR), New Delhi [01(2415)/10/EMR-II]
- RL Fine Chem
- CSIR
A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)(2)6H(2)O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of -halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to -amino acids.
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