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Synthesis of 2,2,2‐Trifluoroethyl Oxazoles, Oxazolines and Furans via Alkyne Oxytrifluoromethylation
Author(s) -
Dong JiaJia,
Zhang SongLin
Publication year - 2020
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.201901405
Subject(s) - chemistry , trifluoromethylation , amide , trifluoromethyl , combinatorial chemistry , alkyne , nucleophile , enol , functional group , substrate (aquarium) , residue (chemistry) , organic chemistry , stereochemistry , catalysis , alkyl , polymer , oceanography , geology
This study reports an oxytrifluoromethylation method for construction of oxazoles and furans motif and the concurrent incorporation of a 2,2,2‐trifluoroethyl group at the aromatic C5‐position. High‐valent copper(III) trifluoromethyl compounds are crucial to this reaction that induces oxy‐trifluoromethylation of alkynes with a pendant amide/enol group functioning as the oxygen‐nucleophile. A wide substrate scope is demonstrated with high efficiency and with broad functional group tolerance. Late‐stage functionalization of dehydrocholic acid, a complex drug compound, is accomplished to show the potential of this method for practical drug design.