Continuous-flow generation of diazoesters and their direct use in S-H and P-H insertion reactions: synthesis of a-sulfanyl, a-sulfonyl and a-phosphono carboxylates

    • Hannah E. Bartrum1
    • David C. Blakemore2
    • Christopher J. Moody1
    • Christopher J. Hayes1
    • 1School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK
    • 2Pfizer Neusentis, The Portway Building, Granta Park, Cambridge, CB21 6GS, UK

    The synthesis of α-sulfanyl, α-sulfonyl, and α-phosphono carboxylates has been achieved using a two-step procedure involving the in-flow generation of diazoesters from sulfonylhydrazones, via Bamford–Stevens elimination, and then subsequent S–H, sulfinate, and P–H carbene insertion reactions. The method for α-sulfonyl ester is particularly noteworthy as it represents a very atom economic (‘green’) way to access the products, and it completely avoids the use of alkyl halides.

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