Aerobic Copper-Catalyzed\nOxysulfonylation of Vinylarenes\nwith Sodium Sulfinates under Mild Conditions: A Modular Synthesis\nof β‑Ketosulfones

An aerobic copper-catalyzed oxysulfonylation of vinylarenes\nwith\nsodium sulfinates is described. This protocol features mild reaction\nconditions, convenient operation, and broad substrate scope with respect\nto vinylarenes and sodium sulfinates. Notably, the protocol demonstrates\nexcellent tolerance of functional groups such as chloro, bromo, ester,\ncyano, and nitro groups. Mechanistic investigations indicated that\nthe reaction should undergo radical cascades involving a sulfonyl\nradical generated from sodium sulfinate with air as the terminal oxidant,\naddition across alkene to deliver a benzylic radical, and subsequent\ncross-coupling with air.

Publication Details

Journal
Figshare
Published
2024-08-21
DOI
https://doi.org/10.1021/acs.joc.4c01660.s001
Primary Topic
Genetic diversity and population structure
Type
article
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article

Aerobic Copper-Catalyzed\nOxysulfonylation of Vinylarenes\nwith Sodium Sulfinates under Mild Conditions: A Modular Synthesis\nof β‑Ketosulfones

Figshare
Genetic diversity and population structure
article

Aerobic Copper-Catalyzed\nOxysulfonylation of Vinylarenes\nwith Sodium Sulfinates under Mild Conditions: A Modular Synthesis\nof β‑Ketosulfones

article en

Abstract

An aerobic copper-catalyzed oxysulfonylation of vinylarenes\nwith\nsodium sulfinates is described. This protocol features mild reaction\nconditions, convenient operation, and broad substrate scope with respect\nto vinylarenes and sodium sulfinates. Notably, the protocol demonstrates\nexcellent tolerance of functional groups such as chloro, bromo, ester,\ncyano, and nitro groups. Mechanistic investigations indicated that\nthe reaction should undergo radical cascades involving a sulfonyl\nradical generated from sodium sulfinate with air as the terminal oxidant,\naddition across alkene to deliver a benzylic radical, and subsequent\ncross-coupling with air.

Figshare
Clean water and sanitation
Openalex Percentile: Top 50%
Genetic diversity and population structure
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Aerobic Copper-Catalyzed\nOxysulfonylation of Vinylarenes\nwith Sodium Sulfinates under Mild Conditions: A Modular Synthesis\nof β‑Ketosulfones · Figshare (2024) | TGRS Research Map | TGRS