Synthesis 2020; 52(15): 2259-2266
DOI: 10.1055/s-0040-1707525
paper
© Georg Thieme Verlag Stuttgart · New York

Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

Dmitry Dar’in
a  Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
,
Grigory Kantin
a  Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
,
Olga Bakulina
a  Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
,
a  Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
b  Laboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskyi prospekt, Peterhof 198504, Russian Federation   Email: m.krasavin@spbu.ru
› Author Affiliations
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.

Supporting Information

 
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