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Electrophilic Cyclizations of 2‐Fluoroalk‐3‐yn‐1‐ones: Room‐Temperature Synthesis of Diversely 2,5‐Disubstituted 3,4‐Fluorohalofurans
Author(s) -
Li Yan,
Wheeler Kraig A.,
Dembinski Roman
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100344
Subject(s) - selectfluor , chemistry , dichloromethane , silylation , zinc bromide , electrophile , bromide , reagent , zinc , n bromosuccinimide , medicinal chemistry , halogenation , electrophilic fluorination , chloride , organic chemistry , combinatorial chemistry , catalysis , solvent
A 5‐ endo ‐ dig halocyclization of 2‐fluoroalk‐3‐yn‐1‐ones with the use of N ‐iodo‐ and N ‐bromosuccinimide, in the presence of gold chloride/zinc bromide (5:20 mol‐%, dichloromethane), under ambient conditions, provides a facile method for the synthesis of 2,5‐disubstituted 3‐bromo‐4‐fluoro‐ and3‐fluoro‐4‐iodofurans. The sequential procedure starts atmonofluorination of the alk‐1‐en‐3‐yn‐1‐yl silyl ethers with Selectfluor and proceeds with good overall yields (62–78 %).