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, UKRead the publication that featured this abstract
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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