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Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones. / Dar'In, Dmitry; Kantin, Grigory; Bakulina, Olga; Krasavin, Mikhail.

In: Synthesis (Germany), Vol. 52, No. 15, 04.08.2020, p. 2259-2266.

Research output: Contribution to journal › Article › peer-review

Harvard

Dar'In, D, Kantin, G, Bakulina, O & Krasavin, M 2020, 'Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones', Synthesis (Germany), vol. 52, no. 15, pp. 2259-2266. https://doi.org/10.1055/s-0040-1707525

APA

Dar'In, D., Kantin, G., Bakulina, O., & Krasavin, M. (2020). Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones. Synthesis (Germany), 52(15), 2259-2266. https://doi.org/10.1055/s-0040-1707525

Vancouver

Dar'In D, Kantin G, Bakulina O, Krasavin M. Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones. Synthesis (Germany). 2020 Aug 4;52(15):2259-2266. https://doi.org/10.1055/s-0040-1707525

Author

Dar'In, Dmitry ; Kantin, Grigory ; Bakulina, Olga ; Krasavin, Mikhail. / Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones. In: Synthesis (Germany). 2020 ; Vol. 52, No. 15. pp. 2259-2266.

BibTeX

@article{59fe12c3b0e84f868bf89d54a6ae7ae1,
title = "Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones",
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.",
keywords = "Aliphatic diazo compounds, diazo ketosulfones, diazo transfer, pyrazole synthesis, Rh(II)-catalyzed cyclization, α-haloketones, DIAZOSULFONES, SULFONYLPYRAZOLES, CYCLOPROPANATION, ALDEHYDES, DIAZOCARBONYL COMPOUNDS, FUNCTIONALIZATION, CYCLOADDITION, REGIOSELECTIVE SYNTHESIS, alpha-haloketones, aliphatic diazo compounds, C-H INSERTION",
author = "Dmitry Dar'In and Grigory Kantin and Olga Bakulina and Mikhail Krasavin",
year = "2020",
month = aug,
day = "4",
doi = "10.1055/s-0040-1707525",
language = "English",
volume = "52",
pages = "2259--2266",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "15",

}

RIS

TY - JOUR

T1 - Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

AU - Dar'In, Dmitry

AU - Kantin, Grigory

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2020/8/4

Y1 - 2020/8/4

N2 - 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.

AB - 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.

KW - Aliphatic diazo compounds

KW - diazo ketosulfones

KW - diazo transfer

KW - pyrazole synthesis

KW - Rh(II)-catalyzed cyclization

KW - α-haloketones

KW - DIAZOSULFONES

KW - SULFONYLPYRAZOLES

KW - CYCLOPROPANATION

KW - ALDEHYDES

KW - DIAZOCARBONYL COMPOUNDS

KW - FUNCTIONALIZATION

KW - CYCLOADDITION

KW - REGIOSELECTIVE SYNTHESIS

KW - alpha-haloketones

KW - aliphatic diazo compounds

KW - C-H INSERTION

UR - http://www.scopus.com/inward/record.url?scp=85089080451&partnerID=8YFLogxK

U2 - 10.1055/s-0040-1707525

DO - 10.1055/s-0040-1707525

M3 - Article

AN - SCOPUS:85089080451

VL - 52

SP - 2259

EP - 2266

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 15

ER -

ID: 62463151