A radical Smiles rearrangement difunctionalization of activated alkenes <i>via</i> desulfonylation and insertion of sulfur dioxide relay strategy

Tian, Si-Wei; Luo, Zhen-Tao; Xiong, Bi-Quan; Tang, Ke-Wen; Huang, Peng-Fei; Liu, Yu

doi:10.1039/d4gc00186a

Green Chem.

2024

DOI: 10.1039/d4gc00186a

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A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy

Si-Wei Tian,

Zhen-Tao Luo,

Bi-Quan Xiong

et al.

Abstract: A visible-light-induced difunctionalization of activated alkenes for building alkylsulfonylated oxindoles and amides through a radical Smiles rearrangement strategy was reported. A tandem SO2 insert/1,4-aryl migration/desulfonylation/cyclization sequence was involved in this...

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Cited by 5 publications

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Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Chen,

Li,

Liu

et al. 2024

Org. Lett.

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A cascade reaction of cyclopropyl alcohols, DABSO (1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate), and N-(sulfonyl)acrylamides has been developed. This tandem process went through a cyclopropanol ring opening and Michael addition sequence. The γ-keto sulfinate generated from the reaction between cyclopropanol and DABSO serves as the nucleophilic reagent, and N-(sulfonyl)acrylamide is used as the Michael addition acceptor. By utilizing this strategy, multitudinous sulfonebridged 1,7-dicarbonyl compounds that contain both a β-sulfonyl amide unit and γ-keto sulfone skeleton were conveniently synthesized.

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Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Chen,

Li,

Liu

et al. 2024

Org. Lett.

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Electron-Donor-Mediated Divergent Transformation of Br–R_F via EDA Complex for the Synthesis of Fluorine-Containing Oxindoles and Amides

Zhang,

Lan,

Yang

et al. 2024

Org. Lett.

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We have developed an unprecedented electrondonor-controlled divergent reaction between N-alkylsulfonylated acrylamides and Br−R F , facilitated by an electron donor−acceptor (EDA) complex, for the synthesis of fluorine-containing oxindoles and amides. Key to this divergent transformation is the EDA complex generation by altering electron donors. This approach has several advantages, such as broad substrate scope, being metalcatalyst-and photocatalyst-free, and having good functional group tolerance.

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Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides

Tian,

Chen,

et al. 2024

Org. Lett.

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A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy

Abstract: A visible-light-induced difunctionalization of activated alkenes for building alkylsulfonylated oxindoles and amides through a radical Smiles rearrangement strategy was reported. A tandem SO2 insert/1,4-aryl migration/desulfonylation/cyclization sequence was involved in this...

Cited by 5 publications

References 84 publications

Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Electron-Donor-Mediated Divergent Transformation of Br–R_F via EDA Complex for the Synthesis of Fluorine-Containing Oxindoles and Amides

Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides

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A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy

Abstract: A visible-light-induced difunctionalization of activated alkenes for building alkylsulfonylated oxindoles and amides through a radical Smiles rearrangement strategy was reported. A tandem SO2 insert/1,4-aryl migration/desulfonylation/cyclization sequence was involved in this...

Cited by 5 publications

References 84 publications

Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Electron-Donor-Mediated Divergent Transformation of Br–RF via EDA Complex for the Synthesis of Fluorine-Containing Oxindoles and Amides

Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides

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Product

Resources

About

Electron-Donor-Mediated Divergent Transformation of Br–R_F via EDA Complex for the Synthesis of Fluorine-Containing Oxindoles and Amides