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

Dmitry Dar’in; Grigory Kantin; Olga Bakulina; Mikhail Krasavin

doi:10.1055/s-0040-1707525

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(15): 2259-2266
DOI: 10.1055/s-0040-1707525

paper

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

Dmitry Dar’in

^aSaint Petersburg State University, Saint Petersburg 199034, Russian Federation

,

Grigory Kantin

^aSaint Petersburg State University, Saint Petersburg 199034, Russian Federation

,

Olga Bakulina

^aSaint Petersburg State University, Saint Petersburg 199034, Russian Federation

,

Mikhail Krasavin ∗

^aSaint Petersburg State University, Saint Petersburg 199034, Russian Federation

^bLaboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskyi prospekt, Peterhof 198504, Russian Federation eMail: m.krasavin@spbu.ru

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Abstract

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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 synthesis

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Referenzen

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