Copper Loading-Controlled Selective Synthesis of 2,5-Bis(trifluoromethyl) and Monotrifluoromethyl-Substituted Oxazoles - Details

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A　general　domino　annulation　reaction　of　sulfonylmethyl　isocyanide　with　trifluoroacetic　anhydride　in　the　presence　of　copper　chloride　as　an　additive　is　developed.　The　reaction　affords　2,5-bis(trifluoromethyl)oxazoles　in　modest　to　good　yields　under　mild　conditions.　A　wide　variety　of　sulfonylmethyl　isocyanide　and　perfluorocarboxylic　anhydride　substrates　are　amenable　to　this　transformation.　Under　a　higher　copper　salt　loading　conditions,　the　reaction　led　to　the　formation　of　monotrifluoromethyl-substituted　oxazole　product.　©　2023　American　Chemical　Society

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[ 1 ] [Wu W.]Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, 350108, China
[ 2 ] [Zhang Z.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Li J.]Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, 350108, China
[ 4 ] [Xia J.]Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, 350108, China
[ 5 ] [Han X.]Testing and Analysis Center, Soochow University, Suzhou, 215123, China
[ 6 ] [Weng Z.]Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, 350108, China
[ 7 ] [Weng Z.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China

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Journal of Organic Chemistry

ISSN： 0022-3263

Year： 2024

Issue： 1

Volume： 89

Page： 589-598

3 . 4 0 0

JCR@2023

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