21984-93-0Relevant articles and documents
A sulfone-based strategy for the preparation of 2,4-disubstituted furan derivatives
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
, p. 8131 - 8137 (2011/11/28)
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 produces the 2,4-disubstituted furans in 60-92% yield. This strategy has been used to prepare rabdoketone A (12) and the naturally occurring nematotoxic furoic acid 13. (Figure presented)
A General Approach to 4-Substitution of 2-Alkylfurans
Nolan, Steven M.,Cohen, Theodore
, p. 2473 - 2476 (2007/10/02)
Treatment of 2-alkylfurans with butyllithium followed by diphenyl disulfide yields 2-(phenylthio)-5-alkylfurans.When the 2-(phenylthio)-3-bromo-5-alkylfurans arising by bromination of the latter are treated with tert-butyllithium, the corresponding 3-lithio derivative is produced and it can be trapped by electrophiles such as alkyl iodides, aldehydes, trimethylsilyl chloride, and carbon dioxide.Raney nickel desulfurization of the product of such trapping produces 4-substituted-2-alkylfurans.
