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An efficient one pot method for the synthesis of α-alkoxymethylphosphonium iodides is developed by using PPh3/I2 combination at room temperature. Reaction conditions are found general to synthesize wide range of structurally variant alkoxymethylphosphonium iodides in high yield (70–91%). These new functionalized phosphonium salts are further used in stereoselective synthesis of vinyl ethers as well as in carbon homologation of aldehydes.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0421-6) contains supplementary material, which is available to authorized users.

The work describes a detailed account of the Lewis acid-catalyzed preparation of structurally variant alkoxymethyl halides. A series of Lewis acids with different halogenating agents areevaluatedfor the cleavage of bis-alkoxymethanes, where several readily available Lewis acids were found to exhibit high catalytic potential. SOCl2 with MgCl2 was found one of the best combinations for facile and efficient preparation of structurally diverse alkoxymethyl halides under solvent-free conditions. The efficacy of the methodology was established to obtain a wide range of mixed acetals through alkoxymethylation of phosphorus, sulfur, nitrogen, and oxygen containing nucleophiles. The present procedure has significant advantages including simplicity, generality, rapidity, and availability of reagents.