Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 5, Pages 2861-2868Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502929x
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Funding
- National Natural Science Foundation of China [21332007, 21472153]
- Program for Changjiang Scholars and Innovative Research Team in University of Ministry of Education, China
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A one-pot reaction for the transformation of common secondary amides into amines with C-C bond formation is described. This method consists of in situ amide activation with Tf2O-partial reduction-addition of C-nucleophiles. The method is general in scope, which allows employing both hard nucleophiles (RMgX, RLi) and soft nucleophiles, as well as enolates. With the use of soft nucleophiles, the reaction proceeded with high chemoselectivity at a secondary amide in the presence of ester, cyano, nitro, and tertiary amide groups.
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