Synthesis of trifluoromethylated amines using 1,1-bis(dimethylamino)-2,2,2-trifluoroethane

Authors
Xu, YL Dolbier, WR
Citation
Yl. Xu et Wr. Dolbier, Synthesis of trifluoromethylated amines using 1,1-bis(dimethylamino)-2,2,2-trifluoroethane, J ORG CHEM, 65(7), 2000, pp. 2134-2137
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
7
Year of publication
2000
Pages
2134 - 2137
Database
ISI
SICI code
0022-3263(20000407)65:7<2134:SOTAU1>2.0.ZU;2-J
Abstract
Lewis acid-catalyzed deamination of aminal, 1,1-bis(dimethylamino)-2,2,2-tr ifluoroethane using ZnI2 in ether, generates the 2,2,2-trifluoro-1,1-dimeth ylaminoethyl carbocation, which undergoes synthetically useful electrophili c reactions with alkynes, a variety of electron-rich alkenes, and TMS cyani de to form trifluoromethylated alkynylamines, homoallylic amines, alpha/bet a-unsaturated ketones, and cyanoamines in fair to good yields.