Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 20, Pages 5014-5020Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob00717b
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Funding
- Foundation of the Department of Education of Guangdong Province [2017KZDXM085, 2016KTSCX144, 2016KCXTD005]
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A novel vicinal aminotrifluoromethylation of alkenes using CF3SO2Na as a trifluoromethyl precursor and acetonitrile as an N-nucleophile has been achieved by an electrooxidative strategy. The present electrochemical protocol achieves efficient and highly regioselective difunctionalization of C-C bonds under metal-free and external oxidant-free electrolysis conditions, leading to a series of ss-trifluoromethylamine compounds with good to excellent yields. It is confirmed that the reaction involves free radical processes since CF3 radicals are trapped by scavengers and the ss-trifluoromethylated radical is trapped by BHT, and the deuterium-labeling experiments prove that the oxygen in the product comes from water.
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