A General Approach to 4-Substitution of 2-Alkylfurans

Article abstract of DOI:10.1021/jo00325a009

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.