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.

C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process

2018 ◽  
Vol 16 (8) ◽  
pp. 1227-1241 ◽  
Author(s):  
Xiaoyan Xu ◽  
Jun Zhang ◽  
Hongguang Xia ◽  
Jie Wu
Keyword(s):  
Reaction Process ◽  
Radical Process ◽  
Mild Conditions ◽  
Recent Advances ◽  
Aminyl Radical

This review is focused on the recent advances in the C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process. Diverse substituted hydrazones including N-heterocycles are afforded under mild conditions with excellent selectivities. In general, an aminyl radical as the key intermediate is involved during the reaction process.

Fixation of sulfur dioxide into small molecules

2015 ◽  
Vol 13 (6) ◽  
pp. 1592-1599 ◽  
Author(s):  
Gang Liu ◽  
Congbin Fan ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Small Molecules ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Radical Process ◽  
Metal Free ◽  
Recent Advances

Recent advances in the insertion of sulfur dioxide under transition metal catalysis or metal-free conditions via a radical process are presented.

Recent advances in sulfonylation reactions using potassium/sodium metabisulfite

2020 ◽  
Vol 56 (30) ◽  
pp. 4145-4155 ◽  
Author(s):  
Shengqing Ye ◽  
Min Yang ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Sodium Metabisulfite ◽  
Metal Catalysis ◽  
Potassium Sodium ◽  
Mild Conditions ◽  
Recent Advances ◽  
Radical Processes

Recently, sulfonylation reactions using potassium/sodium metabisulfite as the sulfur dioxide surrogate have been developed rapidly. In most cases, the transformations go through radical processes with the insertion of sulfur dioxide under mild conditions. Additionally, transition metal catalysis is applied in the reactions for the synthesis of sulfonyl-containing compounds.

Recent advances in the sulfonylation of C–H bonds with the insertion of sulfur dioxide

2018 ◽  
Vol 54 (89) ◽  
pp. 12561-12569 ◽  
Author(s):  
Guanyinsheng Qiu ◽  
Kaida Zhou ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Metal Catalysis ◽  
Radical Process ◽  
Recent Advances

Recent advances in the sulfonylation of C–H bonds with the insertion of sulfur dioxide are summarized. C–H bond sulfonylation under transition metal catalysis or through a radical process has been developed. In some cases, the sulfonylation can be performed under catalyst- and additive-free conditions, or can be facilitated by visible light irradiation. The efficiency is also studied by merging the radical process and metal catalysis.

A metal-free reaction of sulfur dioxide, cyclopropanols and electron-deficient olefins

2020 ◽  
Vol 56 (89) ◽  
pp. 13852-13855
Author(s):  
Chun Zhang ◽  
Jiapian Huang ◽  
Shengqing Ye ◽  
Jie Tang ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Metal Free ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
Efficient Route

An efficient route to γ-keto sulfones through a metal-free reaction of cyclopropanols, sulfur dioxide and electron-deficient olefins is achieved. This reaction proceeds smoothly under mild conditions without the need of a catalyst, oxidant or additive.

Generation of (E)-β-sulfonyl enamines from sulfur dioxide via a radical process

2021 ◽  
Vol 8 (8) ◽  
pp. 1789-1794
Author(s):  
Xiaodong Tu ◽  
Jiapian Huang ◽  
Wenlin Xie ◽  
Tonghao Zhu ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Radical Process ◽  
Three Component Reaction

An iron(ii)-catalyzed three-component reaction of O-acyl oximes, sulfur dioxide, and N-vinylacetamides is accomplished. Diverse (E)-β-sulfonyl enamines are obtained in moderate to good yields by using this protocol with excellent stereoselectivity and regioselectivity.

scholarly journals Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5270
Author(s):  
Zhenbo Yuan ◽  
Xuanzhong Liu ◽  
Changmei Liu ◽  
Yan Zhang ◽  
Yijian Rao
Keyword(s):  
Amino Acids ◽  
Direct Synthesis ◽  
Environmentally Friendly ◽  
Powerful Method ◽  
Rapid Synthesis ◽  
Conservation Of Energy ◽  
Mild Conditions ◽  
Recent Advances ◽  
Recent Developments

Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C–H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C–H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C–H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.

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.

Recent advances in photoinduced trifluoromethylation and difluoroalkylation

2016 ◽  
Vol 3 (9) ◽  
pp. 1163-1185 ◽  
Author(s):  
Xiaolin Pan ◽  
Hongguang Xia ◽  
Jie Wu
Keyword(s):  
Simple Operation ◽  
Mild Conditions ◽  
Recent Advances

Recent advances in photoinduced trifluoromethylation and difluoroalkylation under photocatalysis are summarized. Most of the photoredox reactions proceed efficiently under mild conditions with simple operation. Various fluorinated reagents are developed and applied in different transformations.

A copper(ii)-catalyzed three-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, with alkenes

2016 ◽  
Vol 3 (11) ◽  
pp. 1498-1502 ◽  
Author(s):  
Runyu Mao ◽  
Zheng Yuan ◽  
Rui Zhang ◽  
Yechun Ding ◽  
Xiaona Fan ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Three Component Reaction ◽  
Efficient Route

A three-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, with alkenes catalyzed by copper(ii) bromide is developed, which provides an efficient route to (E)-alkenyl sulfones or allylic sulfones via the insertion of sulfur dioxide.

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