Electrochemical fluorosulfonylation of alkenes to access vicinal fluorinated sulfones derivatives

Zhao, Bin; Pan, Zichen; Zhu, Anqiao; Yue, Yanni; Ma, Mengtao; Xue, Fei

doi:10.1016/j.tet.2022.132651

Cited by 9 publications

(8 citation statements)

References 79 publications

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“…Column chromatography was performed with 300–400 mesh silica gel using flash column techniques. All reagents with the exception of 2 , 3h , and 14 , which were synthesized according to methods described in the literature, were obtained from commercial sources and were used as received.…”

Section: Methodsmentioning

confidence: 99%

Copper-Catalyzed Stereoselective Radical Phosphono-hydrazonation of Alkynes

2022

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A copper-catalyzed stereoselective phosphono-hydrazonation of terminal alkynes with alkyl carbazates and diarylphosphine oxides is described. This methodology provides facile access to a variety of β-hydrazonophosphine oxides in satisfactory yields. The reaction proceeds under mild conditions and exhibits good functional group tolerance. A mechanism featuring persulfate-mediated oxidative generation of phosphinoyl radicals and copper-assisted hydrazonation is proposed.

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Section: Methodsmentioning

confidence: 99%

Copper-Catalyzed Stereoselective Radical Phosphono-hydrazonation of Alkynes

2022

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“…The Xue group reported an electrochemical three-component reaction of alkenes with sulfonyl hydrazides and triethylamine trihydrofluoride (Scheme 65). [136] The sulfonyl radical adds to the alkene to form a carbon radical intermediate, which is then oxidized by the anode to form a carbon cation that finally undergoes nucleophilic attack by triethylamine trihydrofluoride to generate the fluorinated product. The Wang group reported a copper-catalyzed three-component aminofluorination of alkenes using O-benzoylhydroxylamines as alkylamine radical precursors, enabling direct synthesis of various β-fluoroalkylamines (Scheme 66).…”

Section: Scheme 64 Three-component Radical Cyanoalkylfluorination Of ...mentioning

confidence: 99%

“…The Xue group reported an electrochemical three‐component reaction of alkenes with sulfonyl hydrazides and triethylamine trihydrofluoride (Scheme 65). [ 136 ] The sulfonyl radical adds to the alkene to form a carbon radical intermediate, which is then oxidized by the anode to form a carbon cation that finally undergoes nucleophilic attack by triethylamine trihydrofluoride to generate the fluorinated product.…”

Section: Nucleophilic Fluorination Reagentsmentioning

confidence: 99%

Recent Advances in C—F Bond Formation from Carbon‐Centered Radicals

Zhang,

Wang,

Cheng

2024

Chin. J. Chem.

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Comprehensive SummaryConstruction of C–F bonds is a direct and efficient method for introducing fluorine into pharmaceuticals, agrochemicals, and materials. Strategies such as nucleophilic, electrophilic, radical, and transition‐metal catalyzed fluorination have been developed to meet the demand of diverse C–F bond formation. Among them, radical fluorination has been witnessed with substantial advancement in a recent decade. Herein, we reviewed methods for formation of C–F bonds with carbon‐centered radicals as key intermediates, especially in recent five years. We introduce in the paper with different fluorinating reagents, strategies for radical generation, and application in late‐stage functionalization and synthesis of PET tracers. We also indicate the current limitations and propose the direction of the field for the future development.This article is protected by copyright. All rights reserved.

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“…Xue and co‐workers [74] developed an electrochemical fluorosulfonylation 55.1 . Readily available nucleophile Et 3 N ⋅ 3HF was the fluorination reagent.…”

Section: Thiolationmentioning

confidence: 99%

“…Actually, AgNO 3 , AgC 2 O 3 , FeCl 2 , CuCl 2 and CoCl 2 were all able to promote these transformations. A wide array of functional groups with electronic patterns, including halides Xue and co-workers [74] developed an electrochemical fluorosulfonylation 55.1. Readily available nucleophile Et 3 N • 3HF was the fluorination reagent.…”

Section: Rso 2 Nhnh 2 -Mediated Reactionsmentioning

confidence: 99%

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Huang

Wang

et al. 2023

Adv Synth Catal

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Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur-containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three-component reactions. It will reduce the number of steps and waste generation, and form complicated molecules from simple starting materials. Herein, recent developments (2013-2022) have been summarized via two categories: (1) selenylation via seleniranium intermediates or Se-centered radicals;(2) thiolation with more diverse mechanisms and products Reactions with electron-rich arenes, alcohols, water, acids, NaN 3 , amines, KSCN, and sulfamides, TMSNCS, TMSN 3 , Et 3 N • 3HF, SOCl 2 , HCl, NFSI, t BuONO, pyridinium salts, t BuOOH, ArN 2 BF 4 , CO 2 , CO, O 2 , CF 3 SO 2 Cl, R 2 P(O)À H, (RO) 2 P(O)SH, (RO) 2 P(O)OH et al will be discussed.We hope this review will do help for future research in this area.1. Thiolation 3.1. Synthesis of Sulfides 3.2. Synthesis of Sulfoxides 3.3. Synthesis of Sulfones 4.Conclusions and Outlook

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Electrochemical fluorosulfonylation of alkenes to access vicinal fluorinated sulfones derivatives

Cited by 9 publications

References 79 publications

Copper-Catalyzed Stereoselective Radical Phosphono-hydrazonation of Alkynes

Copper-Catalyzed Stereoselective Radical Phosphono-hydrazonation of Alkynes

Recent Advances in C—F Bond Formation from Carbon‐Centered Radicals

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

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