An efficient protocol for the synthesis of highly functionalized furans via intramolecular Wittig reaction has been developed using catalytic amounts of organophosphane and triethylamine. Initial reduction of phosphine oxide by silane resulted in the generation of phosphine, while the decomposition of conjugate acid of Et3N resulted in the regeneration of base, both of which assisted in the formation of the phosphorus ylide. Furthermore, trialkylsilyl chloride served as the trapping agent for the in situ generated silanol, thereby preventing the quenching of acyl chloride. This method tolerated a variety of functionalities such as cyano, ester and keto functions yielding the products in moderate to excellent yields.

Recyclable triethylamine and organophosphane: Synthesis of highly functionalized furan derivatives via catalytic Wittig reaction

251st National Meeting (2016)

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