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Reaction of 1,2‐Unsaturated Trifluoromethyl Ketones and Their Conversion to 1‐(Trifluoromethyl)furan Derivatives
Author(s) -
Zhang Dehui,
Yuan Chengye
Publication year - 2007
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.200700280
Subject(s) - trifluoromethyl , chemistry , furan , aryl , yield (engineering) , phenylacetylene , alcohol , organic chemistry , medicinal chemistry , catalysis , alkyl , materials science , metallurgy
A novel synthetic approach leading to 1‐(trifluoromethyl)furan derivatives is reported. 4‐Aryl‐1,1,1‐trifluorobut‐3‐en‐2‐one was iodinated and subsequently reduced to give the corresponding alcohol. The resultant iodo compound was then subjected to coupling with phenylacetylene to furnish an ( E )‐3‐aryl‐2‐(2‐phenylethynyl)‐1‐(trifluoromethyl)allyl alcohol, which could be cyclized by means of AgOTf to furnish a 2‐(trifluoromethyl)furan in fair yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)