Journal
TETRAHEDRON
Volume 69, Issue 10, Pages 2276-2282Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.01.020
Keywords
Diazoester; Metal carbenoid; S-H Insertion; P-H Insertion; Continuous flow
Categories
Funding
- EPSRC [EP/G027919/1]
- Pfizer
- EPSRC [EP/G027919/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/G027919/1] Funding Source: researchfish
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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.
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