Gold(I)-Catalyzed Cycloisomerization of 2-Fluoroalk-3-yn-1-ones: Synthesis of 2,5-Substituted 3-Fluorofurans

作者：Li Yan; Wheeler Kraig A; Dembinski Roman^*

来源：Advanced Synthesis & Catalysis, 2010, 352(16): 2761-2766.

DOI：10.1002/adsc.201000411

• alkynes
• cyclization
• fluorine
• furans
• gold
• oxygen heterocycles

Fluorination of 1,4-disubstituted tert-butyldimethylsilyl but-1-en-3-yn-1-yl ethers with Selectfluor gives 2-mono-fluorobut-3-yn-1-ones. Subsequent 5-endo-dig cyclization in the presence of chlorotriphenylphosphine gold(I)/silver trifluoromethanesulfonate (both 5 mol%, dichloromethane) under ambient conditions, provides a facile method for the generation of mainly 2,5-diaryl-substituted 3-fluorofurans in high yields (89-96%). The structure of 2-(4-bromophenyl)-3-fluoro-5-(4-methylphenyl) furan was confirmed by X-ray crystallography.

• 出版日期2010-11-2