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Synthesis of 3-Trifluoroethylfurans by Palladium-Catalyzed Cyclization-Isomerization of (Z)-2-Alkynyl-3-trifluoromethyl Allylic Alcohols

Feng-Ling Qing*, Wen-Zhong Gao and Jiewen Ying

*Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Email:

F.-L. Qing, W.-Z. Gao, J. Ying, J. Org. Chem., 2000, 65, 2003-2006.

DOI: 10.1021/jo991463u (free Supporting Information)

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A regio- and stereoselective hydroiodonation of trifluoromethyl propargylic alcohols produces (Z)-2-iodo-3-trifluoromethyl allylic alcohols in good yields. A Pd(PPh3)4-mediated coupling with terminal alkynes provides (Z)-2-alkynyl-3-trifluoromethyl allylic alcohols, which cyclize and subsequently isomerize to 3-trifluoroethylfurans in the presence of PdCl2(CH2CN)2 in THF at 5-10 C.

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ID: J42-Y2000