Electrochemically Induced Synthesis of β‐Ketosulfones from Enol Acetates and Sodium Sulfinates

Electrochemically Induced Synthesis of β‐Ketosulfones from Enol Acetates and Sodium Sulfinates Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2024, Volume: 9, Number: 36, Article number : e202403708, Pages count : DOI: 10.1002/slct.202403708

Authors

Zaikina Lada A. ^1,2 , Mulina Olga M. ² , Merkulova Valentina M. ² , Ilovaisky Alexey I. ² , Vil’ Vera A. ² , Terent'ev Alexander O. ^1,2

Affiliations

1	Mendeleev University of Chemical Technology of Russia 9 Miusskaya Square Moscow 125047 Russian Federation
2	Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky Prospect Moscow 119991 Russian Federation

β-Ketosulfones were synthesized from enol acetates and sodium sulfinates under electrochemical conditions. The starting sulfinates can act both as the supporting electrolyte and as the source of S-centered radicals, allowing electrolysis to proceed without external salt. Side reactions of enol acetates’ oxidation are not observed, and the developed process is quite selective. The proposed electrochemical sulfonylation is compatible with a wide range of the initial enol acetates and sulfinates. On the basis of literature data, control experiments, and CV studies, the presumable reaction pathway is suggested. The key intermediates are S-centered sulfonyl radical, C-centered benzylic radical, and β-acetoxy-β-hydroxysulfone.

Zaikina L.A. , Mulina O.M. , Merkulova V.M. , Ilovaisky A.I. , Vil’ V.A. , Terent'ev A.O.
Electrochemically Induced Synthesis of β‐Ketosulfones from Enol Acetates and Sodium Sulfinates
ChemistrySelect. 2024. V.9. N36. e202403708 . DOI: 10.1002/slct.202403708 Scopus OpenAlex

Scopus:	2-s2.0-85204703816
OpenAlex:	W4402745699

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