Synthesis of Trifluoromethylated Amines Using 1,1-Bis(dimethylamino)-2,2,2-trifluoroethane
The Journal of Organic ChemistryPublished 16 March 2000
Yuelian Xu, William R. Dolbier
Citations36
SJR quartileQ2
SJR score0.74
SNIP0.86
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TL;DR
The 2,2,2-trifluoro-1,1-dimethylaminoethyl carbocation undergoes synthetically useful electrophilic reactions with alkynes, a variety of electron-rich alkenes, and TMS cyanide to form trifluoromethylated alkynylamines, homoallylic amines, alpha,beta-unsaturated ketones, and cyanoamines in fair to good yields.
Abstract
Lewis acid-catalyzed deamination of aminal, 1,1-bis(dimethylamino)-2,2,2-trifluoroethane, using ZnI2 in ether, generates the 2,2,2-trifluoro-1,1-dimethylaminoethyl carbocation, which undergoes synthetically useful electrophilic reactions with alkynes, a variety of electron-rich alkenes, and TMS cyanide to form trifluoromethylated alkynylamines, homoallylic amines, alpha,beta-unsaturated ketones, and cyanoamines in fair to good yields.
Keywords
Pharmacology, Toxicology and Pharmaceutics
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