- A sulfone-based strategy for the preparation of 2,4-disubstituted furan derivatives
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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)
- 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
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p. 8131 - 8137
(2011/11/28)
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- Novel aerobic oxidation of primary sulfones to carboxylic acids
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Primary alkyl aryl sulfones are converted to the corresponding carboxylic acids in fair to excellent yield through double deprotonation and exposure to atmospheric oxygen. The methodology allows for the convenient synthesis of 13C labeled carboxylic acids.
- Bonaparte, Amy C.,Betush, Matthew P.,Panseri, Bettina M.,Mastarone, Daniel J.,Murphy, Ryan K.,Murphree, S. Shaun
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supporting information; experimental part
p. 1447 - 1449
(2011/05/08)
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- A General Approach to 4-Substitution of 2-Alkylfurans
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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.
- Nolan, Steven M.,Cohen, Theodore
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p. 2473 - 2476
(2007/10/02)
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