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

The synthesis of alpha-sulfanyl, alpha-sulfonyl, and alpha-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 alpha-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. (C) 2013 Elsevier Ltd. All rights reserved.