A copper-catalyzed insertion of sulfur dioxide via radical coupling

2020 ◽  
Vol 56 (21) ◽  
pp. 3225-3228 ◽  
Author(s):  
Jun Zhang ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Radical Coupling ◽  
Mild Conditions

A copper-catalyzed reaction of O-acyl oximes, DABCO·(SO2)2, and 2H-azirines is developed under mild conditions, leading to diverse tetrasubstituted β-sulfonyl N-unprotected enamines with excellent stereoselectivity and regioselectivity.

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

Insertion of sulfur dioxide via a radical process: an efficient route to sulfonyl compounds

2018 ◽  
Vol 5 (4) ◽  
pp. 691-705 ◽  
Author(s):  
Guanyinsheng Qiu ◽  
Kaida Zhou ◽  
Liang Gao ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Radical Process ◽  
Mild Conditions ◽  
Recent Advances ◽  
Efficient Route

This review is focused on the recent advances in the chemistry of sulfur dioxide fixation through a radical process. Diverse sulfonyl compounds can be obtained efficiently under mild conditions.

Photoredox-catalyzed sulfonylation of alkyl iodides, sulfur dioxide, and electron-deficient alkenes

2019 ◽  
Vol 55 (15) ◽  
pp. 2214-2217 ◽  
Author(s):  
Shengqing Ye ◽  
Danqing Zheng ◽  
Jie Wu ◽  
Guanyinsheng Qiu
Keyword(s):  
Sulfur Dioxide ◽  
Functional Groups ◽  
Mild Conditions ◽  
Alkyl Iodides

A photoredox-catalyzed sulfonylation of alkyl iodides, sulfur dioxide, and electron-deficient alkenes under mild conditions is achieved. Various functional groups including nitro, halo, acetyl, sufonyl, and pyridinyl are all tolerated under the photoredox conditions.

Photocatalytic three-component radical cascade: a general route to heterocyclic-substituted alkyl sulfones

2021 ◽  
Author(s):  
Jian-Qiang Chen ◽  
Nana Liu ◽  
Qian Hu ◽  
Jin Liu ◽  
Junwei Wu ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Cascade Reaction ◽  
Mild Conditions ◽  
Radical Cascade

A photoredox-catalyzed three-component radical cascade reaction of β,γ-unsaturated oximes/hydrazones, sulfur dioxide surrogate of DABCO·(SO2)2, and alkenes under mild conditions is developed, affording diverse isoxazoline/dihydropyrazole-substituted aliphatic sulfones in good to excellent...

C–H bond sulfonylation of anilines with the insertion of sulfur dioxide under metal-free conditions

2018 ◽  
Vol 54 (54) ◽  
pp. 7459-7462 ◽  
Author(s):  
Kaida Zhou ◽  
Jun Zhang ◽  
Lifang Lai ◽  
Jiang Cheng ◽  
Jiangtao Sun ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Metal Catalysts ◽  
Metal Free ◽  
Mild Conditions ◽  
Three Component Reaction

2-Sulfonylanilines are generated in moderate to good yields through a three-component reaction of anilines, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions. No metal catalysts or additives are needed for this transformation.

Photoredox-catalyzed sulfonylation of difluoroenoxysilanes with the insertion of sulfur dioxide

2020 ◽  
Vol 56 (66) ◽  
pp. 9469-9472 ◽  
Author(s):  
Fu-Sheng He ◽  
Yanfang Yao ◽  
Wenlin Xie ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Sodium Metabisulfite ◽  
Silyl Ethers ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Enol Silyl Ethers

A photoredox-catalyzed three-component reaction of aryldiazonium tetrafluoroborates with sodium metabisulfite and 2,2-difluoro enol silyl ethers is described, providing α,α-difluoro-β-ketosulfones in moderate to good yields under mild conditions.

Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

2019 ◽  
Vol 6 (4) ◽  
pp. 447-450 ◽  
Author(s):  
Qiongzhen Lin ◽  
Yongan Liu ◽  
Zhiwei Xiao ◽  
Liping Zheng ◽  
Xiumiao Zhou ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Functional Group ◽  
Mild Conditions ◽  
Silver Fluoride

Reaction of unactivated alkenes affords various fluoroalkyl-containing alkyl sulfonyl fluorides with good functional group tolerance under mild conditions.

scholarly journals Construction of sterically congested oxindole derivatives via visible-light-induced radical-coupling

2021 ◽  
Author(s):  
Yanling Shen ◽  
Ning Lei ◽  
Cong Lu ◽  
Dailin Xi ◽  
Xinxin Geng ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Modular Assembly ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Broad Scope

Simple, modular assembly of complex fluoroalkyl-containing oxindole derivatives with a broad scope and excellent functional group tolerance under mild conditions (metal- and photocatalyst-free). Benzyl iodides were identified as key intermediates.

Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide

2018 ◽  
Vol 5 (21) ◽  
pp. 3153-3157 ◽  
Author(s):  
Tong Liu ◽  
Yechun Ding ◽  
Xiaona Fan ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Photoinduced Synthesis

Under visible light irradiation, a three-component reaction of potassium alkyltrifluoroborates, sulfur dioxide and alkynes with the assistance of photocatalysis and in the presence of copper(ii) triflate is described. This transformation affords (E)-vinyl sulfones efficiently with excellent regioselectivity and stereoselectivity under mild conditions.

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