Research Progress of Electrochemical Synthesis of <i>C</i>-Sulfonyl Compounds

Wei, Wan-Jie; Zhan, Lei; Gao, Lei; Huang, Guobao; Ma, Xiangyi

doi:10.6023/cjoc202205018

Cited by 8 publications

(2 citation statements)

References 58 publications

(17 reference statements)

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“…Based on these and earlier research findings, [ 13 ] we propose the reaction mechanism depicted in Figure 2. Initially, single‐ electron‐transfer (SET) oxidation of 2a at the anode generates a sulfonyl radical A that reacts with elemental selenium to produce the free radical intermediate TsSe• ( B ).…”

Section: Resultssupporting

confidence: 65%

Electrocatalytic Multicomponent Cascade Cross‐Coupling for the Synthesis of Chalcogenosulfonates

Zhao,

Yan,

Zhou

et al. 2024

Chin. J. Chem.

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Section: Resultssupporting

confidence: 65%

Electrocatalytic Multicomponent Cascade Cross‐Coupling for the Synthesis of Chalcogenosulfonates

Zhao,

Yan,

Zhou

et al. 2024

Chin. J. Chem.

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“…Curve d shows an oxidation peak for indole 1a at 1.32 V. However, in the absence of TBAI, no desired product 3aa could be detected (Table 1, entry 14), which might exclude 1a' as the intermediate of this electrocatalytic transformation (Scheme 7E). Based on these findings and those of previous studies, [13] we propose the reaction mechanism depicted in Scheme 8. Initially, single-electron-transfer (SET) oxidation of 2a at the anode generates a sulfonyl radicalA that reacts with elemental selenium to generate the free radical intermediate TsSe* (B ).…”

Section: Scheme 7 Investigation Of the Mechanismsupporting

confidence: 75%

Electrocatalytic Multicomponent Cascade Cross-Coupling for Synthesis of Chalcogenosulfonates

Zhao,

Yan,

Zhou

et al. 2024

Preprint

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An method for the electrochemical synthesis of chalcogenosulfonates via a tandem multi-component reaction has been developed. This method is performed in an undivided cell without the requirement of external oxidants, acids, and transition metals. A variety of indoles and sulfinic acid sodium salts can be used in this method, and it is effective for the late-stage modifications of complex molecules. Not only thiosulfonates and selenosulfonates but also sulfonotelluroates could be prepared, making this protocol a useful tool for the devel-opment of new functional molecules. The afforded products are promising for pesticide development.

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Supporting Electrolyte‐Free Electrochemical Oxidative C−H Sulfonylation and Thiocyanation of Fused Pyrimidin‐4‐Ones in an All‐Green Electrolytic System

Biswas,

Ghosh,

Das

2023

Chemistry A European J

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An electrooxidative C−H functionalization is a widely accepted route to obtain sulfur‐containing arenes and heteroarenes. However, this process often involves using non‐recyclable supporting electrolytes, (co)solvents like hexafluoroisopropanol, additives like acid, or catalysts. The use of additional reagents can increase costs and waste, reducing atom efficiency. Moreover, unlike other nitrogen‐containing heterocycles, there have only been sporadic reports of electrochemical C−H functionalization in fused pyrimidin‐4‐ones, and an electrolyte‐free process has yet to be developed. This work demonstrates that such anodic coupling reactions can be performed in an all‐green electrolytic system without using such additional electrolytes or HFIP, maintaining a high atom economy. This C−H functionalization strategy utilizes inexpensive sodium sulfinates and ammonium thiocyanate as sulfonylating and thiocyanating agents in an undivided cell at a constant current, using a mixture of CH3CN/H2O as solvent at room temperature. Thus, fused pyrimidin‐4‐ones can be selectively converted into C3‐sulfonylated and ‐thiocyanated derivatives in moderate to good yields.

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Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds

Abstract: 按照电化学合成 C(sp)-磺酰基化合物、C(sp 2 )-磺酰基化合物以及 C(sp 3

Cited by 8 publications

References 58 publications

Electrocatalytic Multicomponent Cascade Cross‐Coupling for the Synthesis of Chalcogenosulfonates

Electrocatalytic Multicomponent Cascade Cross‐Coupling for the Synthesis of Chalcogenosulfonates

Electrocatalytic Multicomponent Cascade Cross-Coupling for Synthesis of Chalcogenosulfonates

Supporting Electrolyte‐Free Electrochemical Oxidative C−H Sulfonylation and Thiocyanation of Fused Pyrimidin‐4‐Ones in an All‐Green Electrolytic System

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