Zirconium-Catalyzed Synthesis of 6-(Trifluoromethyl)-2H-pyran-2-ones via C-C Bond Cleavage - Details

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Zhang, Z. (Zhang, Z..) ^[1] | Huang, Y. (Huang, Y..) ^[2] | Yuan, Z. (Yuan, Z..) ^[3] | Xia, J. (Xia, J..) ^[4] | Weng, Z. (Weng, Z..) ^[5]

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Abstract：

A　strategy　for　the　annulation　reaction　of　alkynones　with　ethyl　4,4,4-trifluoro-3-oxobutanoate　through　C-C　bond　cleavage　is　described.　The　zirconium-catalyzed　transformation　provides　access　to　a　wide　range　of　structurally　diverse　6-(trifluoromethyl)-2H-pyran-2-ones　in　moderate　to　good　yields,　utilizing　Na2CO3　as　a　base.　Further　transformations　into　trifluoromethylated　arene　derivatives　have　been　demonstrated　as　well.　Furthermore,　plausible　reaction　pathways　are　proposed　by　conducting　various　control　experiments　and　isolating　a　β-diketone　intermediate　(X-ray)　containing　an　intramolecular　hydrogen　bond.　©　2024　American　Chemical　Society.

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[ 1 ] [Zhang 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
[ 2 ] [Zhang Z.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Huang Y.]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 ] [Yuan Z.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 5 ] [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
[ 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： 8

Volume： 89

Page： 5683-5689

3 . 4 0 0

JCR@2023

CAS Journal Grade：2

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