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Gold(I)‐Catalyzed Cycloisomerization of 2‐Fluoroalk‐3‐yn‐1‐ones: Synthesis of 2,5‐Substituted 3‐Fluorofurans
Author(s) -
Li Yan,
Wheeler Kraig A.,
Dembinski Roman
Publication year - 2010
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.201000411
Subject(s) - cycloisomerization , chemistry , selectfluor , dichloromethane , trifluoromethanesulfonate , catalysis , furan , medicinal chemistry , organic chemistry , combinatorial chemistry , solvent
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.