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

Li Yan | Zendy; Wheeler Kraig A. | Zendy; Dembinski Roman | Zendy

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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.

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