We have developed a formal phosphine Pummerer reaction that efficiently produces thioalkyl phosphonium salts [1]. Wittig olefination with these salts gives rise to a wide array of vinyl sulfides. We have prepared a wide range of vinyl sulfides from (alkylthioalkyl)triphenylphosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides yields ketones and thereby offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones. This presentation will describe the development of this chemistry and its applications in our laboratory including variations of this methodology that are proving to be useful for the efficient synthesis of heterocyclic scaffolds.

Using thioalkyl phosphonium salts for efficient one-carbon homologation of aldehydes to ketones

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ACS Fall 2022

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