Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 6, Pages 2216-2223Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08219
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Funding
- MINECO [CTQ2014-52769-C3-1-R, CTQ2013-42106-P, CTQ2014-57761-R]
- FPI fellowship
- European Research Council (Advanced Grant) [321066]
- European Research Council (ERC) [321066] Funding Source: European Research Council (ERC)
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Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N bond formation were exclusively formed. Theoretical mechanistic studies have shown that this selective N-amidation reaction proceeds through triplet silver nitrenes.
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