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Transition Metal‐Free Trifluoromethylation of N ‐Allylamides with Sodium Trifluoromethanesulfinate: Synthesis of Trifluoromethyl‐Containing Oxazolines
Author(s) -
Yu Jipan,
Yang Haijun,
Fu Hua
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400144
Subject(s) - trifluoromethylation , chemistry , trifluoromethyl , iodobenzene , intramolecular force , transition metal , intermolecular force , organic chemistry , combinatorial chemistry , sodium , molecule , catalysis , alkyl
A transition metal‐free method for the trifluoromethylation of N ‐allylamides has been developed, and the corresponding trifluoromethyl‐containing oxazolines were prepared in moderate to good yields. The protocol uses readily available substituted N ‐allylamides as the starting materials, inexpensive and easily stored sodium trifluoromethanesulfinate as the trifluoromethyl source, iodobenzene diacetate as the oxidant, and the procedure involves sequential intermolecular trifluoromethylation of alkenes with sodium trifluoromethanesulfinate and intramolecular cyclization. This is the first example to prepare CF 3 ‐containing oxazolines. Therefore, the present method should afford an efficient and practical strategy for synthesis of other CF 3 ‐containing cyclic compounds.