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Synthesis 2020; 52(15): 2259-2266
DOI: 10.1055/s-0040-1707525
DOI: 10.1055/s-0040-1707525
paper
Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
This work was supported by the Russian Foundation for Basic Research (project grant 19-03-00775).Further Information
Publication History
Received: 01 March 2020
Accepted after revision: 01 April 2020
Publication Date:
28 April 2020 (online)
Abstract
A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the ‘sulfonyl-azide-free’ (‘SAFE’) protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.
Key words
aliphatic diazo compounds - diazo ketosulfones - diazo transfer - α-haloketones - Rh(II)-catalyzed cyclization - pyrazole synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707525.
- Supporting Information
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For recent reviews on diazo chemistry, see: