A Sulfone-Based Strategy for the Preparation of 2, 4-Disubstituted Furan Derivatives

…, WJ Andrews, DA Carlson, RM Harrington…

Index: Haines, Nathan R.; VanZanten, Aaron N.; Cuneo, Anthony A.; Miller, John R.; Andrews, William J.; Carlson, David A.; Harrington, Ryan M.; Kiefer, Adam M.; Mason, Jeremy D.; Pigza, Julie A.; Shaun Murphree Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 8131 - 8137

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Citation Number: 8

Abstract

2, 4-Disubstituted furans are prepared by treating 2, 3-dibromo-1-phenylsulfonyl-1-propene (DBP, 2) with 1, 3-diketones under basic conditions. The furan-forming step involves a deacetylation, and the selectivity of this process depends upon the steric demand of the R group. The substituent in position 4 is elaborated by reaction of sulfonyl carbanions with alkyl halides, acyl halides, and aldehydes. Oxidative or reductive desulfonylation ...