Synthesis of α‐Sulfonyl Ketones through a Salicylic Acid‐Catalyzed Multicomponent Reaction Involving Arylsulfonation and Oxidation

An N-heterocyclic carbene (NHC)-catalyzed facile assembly of α-sulfonyl ketones has been successfully developed through a radical-mediated sulfonyl methylation of readily available aldehydes. This protocol involves the effective single-electron transfer reduction of α-iodosulfones by NHC-bound Breslow intermediates, thus allowing a subsequent radical−radical coupling to afford the target compounds. Moreover, the catalytic system was found to be equally effective for difunctionalization of styrenes and 1,3-enynes via a three-component radical relay process.α-Sulfonyl ketones (or β-keto sulfones), as an important type of building block, have been widely applied in synthesizing various organic functional materials and pharmaceuticals (Scheme 1A). 1 In particular, some α-sulfonyl ketones exhibit important biological activities, such as antipyretic and anticholinesterase activity 2 and antibacterial activity, 3 and these compounds have also been used as inhibitors of hydroxysteroid dehydrogenase type I. 4 Thus, substantial effort

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NHC-Catalyzed Synthesis of α-Sulfonyl Ketones via Radical-Mediated Sulfonyl Methylation of Aldehydes

Liu

Zheng

Jialingbieke

et al. 2023

Org. Lett.

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Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SO₂ Surrogate

Pincekova,

Merot,

Schäfer

et al. 2024

Org. Lett.

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Sulfonyl chlorides not only play a crucial role in protecting group chemistry but also are important starting materials in the synthesis of sulfonamides, which are in-demand motifs in drug discovery chemistry. Despite their importance, the number of different synthetic approaches to sulfonyl chlorides is limited, and most of them rely on traditional oxidative chlorination chemistry from thiol precursors. In this report, we disclose a novel Sandmeyer-type sulfonyl chloride synthesis from feedstock anilines and DABSO, used as a stable SO 2 surrogate, in the presence of HCl and a Cu catalyst. The method works on a wide range of anilines and allows for the isolation of the sulfonyl chloride after aqueous workup or its direct conversion into the sulfonamide by simple addition of an amine after the completion of the Sandmeyer reaction. The scalability of this method was demonstrated on a 20 g scale, and the corresponding heterocyclic sulfonyl chloride was isolated in 80% yield and excellent purity.

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Synthesis of α‐Sulfonyl Ketones through a Salicylic Acid‐Catalyzed Multicomponent Reaction Involving Arylsulfonation and Oxidation

Cited by 2 publications

References 72 publications

NHC-Catalyzed Synthesis of α-Sulfonyl Ketones via Radical-Mediated Sulfonyl Methylation of Aldehydes

NHC-Catalyzed Synthesis of α-Sulfonyl Ketones via Radical-Mediated Sulfonyl Methylation of Aldehydes

Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SO₂ Surrogate

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Synthesis of α‐Sulfonyl Ketones through a Salicylic Acid‐Catalyzed Multicomponent Reaction Involving Arylsulfonation and Oxidation

Cited by 2 publications

References 72 publications

NHC-Catalyzed Synthesis of α-Sulfonyl Ketones via Radical-Mediated Sulfonyl Methylation of Aldehydes

NHC-Catalyzed Synthesis of α-Sulfonyl Ketones via Radical-Mediated Sulfonyl Methylation of Aldehydes

Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SO2 Surrogate

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Product

Resources

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Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SO₂ Surrogate