Formal allylic C(sp<sup>3</sup>)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Wen, Jian; Zou, Liang‐Hua; Shao, Zeyu; Zhou, Junqi; Wang, Ziyu; Liu, Biao; Wang, Cheng

doi:10.1039/d3qo00459g

Cited by 6 publications

(1 citation statement)

References 44 publications

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“…To the best of our knowledge, a strategy based on the ring-opening of cyclic sulfonium salts to establish primary alcohols has not been reported. As part of our ongoing interest in exploring the multiple reactivities of alkenyl sulfonium salts . Herein, we first report a practical and effective strategy for the synthesis of sulfur-containing primary alcohol compounds via base-promoted ring-opening hydroxylation of cyclic sulfonium salts.…”

Section: Introductionmentioning

confidence: 99%

Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Wang,

Shao,

Wang

et al. 2024

J. Org. Chem.

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Herein, we reported a general strategy for the synthesis of sulfur-containing primary alcohol derivatives by base-promoted ringopening hydroxylation of cyclic sulfonium salts. A variety of sulfonium salts were successfully transformed into the desired hydroxylated products in moderate to excellent yields with good functional group tolerance. Moreover, the one-pot synthesis, scale-up reaction, and late-stage functionalization of complex molecules demonstrated the practicability of this synthetic protocol in the field of synthetic chemistry.

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Section: Introductionmentioning

confidence: 99%

Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Wang,

Shao,

Wang

et al. 2024

J. Org. Chem.

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Direct Site‐Selective Difunctionalization of Pyrazoles

Liu,

Wang,

Wang

et al. 2024

Adv Synth Catal

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Herein, we first report a novel and efficient protocol for the direct site‐selective difunctionalization of pyrazoles under mild reaction conditions. This protocol exhibits exceptional site‐selectivity and demonstrates a broad substrate scope. In‐depth mechanistic studies elucidate the dual role of the sulfonium salt as both the reaction substrate and acid donor, effectively promoting the reaction. The demonstrated one‐pot synthesis, scale‐up reaction and further modifications of product will help to promote the potential application of this protocol in organic synthesis and related fields.

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Base‐Promoted Selective Synthesis of Alkynyl Sulfides via C−S Bond Cleavage of Alkynyl Sulfonium Salts

Wang,

Su,

et al. 2024

Adv Synth Catal

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An effective one‐pot approach has been devised for the selective synthesis of alkynyl sulfides through the cleavage of C−S bonds in alkynyl sulfonium salts. This method involves a base‐promoted nucleophilic ring‐opening and desulfurization pathway, enabling the efficient preparation of diverse alkynyl sulfide compounds. The reaction demonstrates excellent tolerance to various functional groups and proves applicable to the late‐stage functionalization of bioactive molecules and pharmaceuticals. Moreover, the practicality of this method has been underscored through scale‐up reaction and modification of alkynyl sulfide products.

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Formal allylic C(sp³)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Abstract: Metal-free allylic C(sp3)−H alkylation of branched α-styryl sulfonium salts based on [2,3]-sigmatropic rearrangement strategies has been developed. This operationally simple protocol enables allylic C(sp3)−H alkylation of a wide range of...

Cited by 6 publications

References 44 publications

Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Direct Site‐Selective Difunctionalization of Pyrazoles

Base‐Promoted Selective Synthesis of Alkynyl Sulfides via C−S Bond Cleavage of Alkynyl Sulfonium Salts

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Formal allylic C(sp3)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Abstract: Metal-free allylic C(sp3)−H alkylation of branched α-styryl sulfonium salts based on [2,3]-sigmatropic rearrangement strategies has been developed. This operationally simple protocol enables allylic C(sp3)−H alkylation of a wide range of...

Cited by 6 publications

References 44 publications

Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Direct Site‐Selective Difunctionalization of Pyrazoles

Base‐Promoted Selective Synthesis of Alkynyl Sulfides via C−S Bond Cleavage of Alkynyl Sulfonium Salts

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Formal allylic C(sp³)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts