期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 37, 页码 12817-12819出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja105194s
关键词
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资金
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Research Chair
- Canada Foundation for Innovation
- Universite de Montreal
- FQRNT
This communication describes a metal-free methodology involving an efficient and controlled reduction of secondary amides to imines, aldehydes, and amines in good to excellent yields under ambient pressure and temperature. The process includes a chemoselective activation of a secondary amide with triflic anhydride in the presence of 2-fluoropyridine. The electrophilic activated amide can then be reduced to the corresponding iminium using triethylsilane, a cheap, rather inert, and commercially available reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed via a sequential reductive amination by the addition of silane and Hantzsch ester hydride in a one-pot reaction. Moreover, this reduction tolerates various functional groups that are usually reactive under reductive conditions and is very selective to secondary amides.
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