ZnI2-Catalyzed Aminotrifluoromethylation Cyclization of Alkenes Using PhICF3Cl

We report here an alternatively catalytic aminotrifluoromethylation of alkenes using PhICF3Cl as a bifunctional reagent along with ZnI2 as a dual catalyst. A combined catalytic strategy was established for the intramolecular aminotrifluoromethylation of 4-pentenamines. As a result, a set of 2-triflu...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 2; pp. 1987 - 1999
Main Authors Huang, Wanqiao, Xu, Cong, Yu, Jianxin, Wang, Mang
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.01.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OLEFINS
AMINATION
TRIFLUOROMETHYLATION REACTIONS
HETEROCYCLES
UNACTIVATED ALKENES
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Summary:We report here an alternatively catalytic aminotrifluoromethylation of alkenes using PhICF3Cl as a bifunctional reagent along with ZnI2 as a dual catalyst. A combined catalytic strategy was established for the intramolecular aminotrifluoromethylation of 4-pentenamines. As a result, a set of 2-trifluoroethyl-pyrrolidines was obtained in a high selectivity. Mechanism studies revealed that the reaction included an iodine anion-catalyzed radical chlorotrifluoromethylation of alkenes and a sequential Lewis acid-promoted aminocyclization of the resulting chlorotrifluoromethylated intermediates.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02637