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

Guanyinsheng Qiu; Kaida Zhou; Liang Gao; Jie Wu

doi:10.1039/c7qo01073g

journal article Jan 01, 2018

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

Guanyinsheng Qiu Kaida Zhou Liang Gao

Jie Wu

Organic Chemistry Frontiers Vol. 5 No. 4 pp. 691-705 · Royal Society of Chemistry (RSC)

View at Publisher Save 10.1039/c7qo01073g

Abstract

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.

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References

109

[1]

M. Bartholow , Top 200 Drugs of 2011. Pharmacy Times. http://www.pharmacytimes.com/publications/issue/2012/July2012/Top-200-Drugs-of-2011

[2]

For a list of the top drugs by year, see: http://cbc.arizona.edu/njardarson/group/toppharmaceuticals-poster

[3]

Drug Discovery: A Historical Perspective

Jürgen Drews

Science 2000 10.1126/science.287.5460.1960

[4]

Deeming Org. Lett. (2014) 10.1021/ol403122a

[5]

Rocke Org. Lett. (2014) 10.1021/ol4031233

[6]

Emmett Angew. Chem., Int. Ed. (2013) 10.1002/anie.201305369

[7]

Dong Angew. Chem., Int. Ed. (2017) 10.1002/anie.201702292

[8]

Zhang Angew. Chem., Int. Ed. (2011) 10.1002/anie.201101341

[9]

Li Sci. China: Chem. (2017) 10.1007/s11426-016-0473-5

[10]

Zhang Chin. J. Org. Chem. (2016) 10.6023/cjoc201603014

[11]

Nguyen J. Am. Chem. Soc. (2010) 10.1021/ja1081124

[12]

Ye Chem. Commun. (2012) 10.1039/c2cc33725h

[13]

Ye Adv. Synth. Catal. (2014) 10.1002/adsc.201400334

[14]

An Org. Biomol. Chem. (2016) 10.1039/c5ob02514a

[15]

Johnson Angew. Chem., Int. Ed. (2014) 10.1002/anie.201400037

[16]

Mao Org. Chem. Front. (2016) 10.1039/c6qo00070c

[17]

Wang Org. Lett. (2014) 10.1021/ol5018849

[18]

Zheng Org. Chem. Front. (2016) 10.1039/c5qo00399g

[19]

Zheng Org. Chem. Front. (2016) 10.1039/c6qo00099a

[20]

Ye Chem. Commun. (2012) 10.1039/c2cc34957d

[21]

Li Eur. J. Org. Chem. (2014) 10.1002/ejoc.201402212

[22]

Liu Org. Biomol. Chem. (2015) 10.1039/c4ob02139h

[23]

Bisseret Org. Biomol. Chem. (2013) 10.1039/c3ob40997j

[24]

Deeming Synthesis (2014)

[25]

Emmett Asian J. Org. Chem. (2015) 10.1002/ajoc.201500103

[26]

D. Zheng and J.Wu , Sulfur Dioxide Insertion Reactions for Organic Synthesis , Nature Springer , Berlin , 2017 10.1007/978-981-10-4202-7

[27]

Richards-Taylor Chem. Sci. (2014) 10.1039/c3sc52332b

[28]

Zhang Chem. Commun. (2016) 10.1039/c5cc09830k

[29]

Du Asian J. Org. Chem. (2017) 10.1002/ajoc.201600518

[30]

P. Renaud and M. P.Sibi , Radicals in Organic Synthesis , Wiley-VCH Verlag GmbH , Weinheim, Germany , 2001 10.1002/9783527618293

[31]

Tsai J. Org. Chem. (1998) 10.1021/jo9718915

[32]

Hwang J. Polym. Sci., Part A: Polym. Chem. (1993) 10.1002/pola.1993.080310608

[33]

Kharasch J. Org. Chem. (1948) 10.1021/jo01164a017

[34]

Good Trans. Faraday Soc. (1967) 10.1039/tf9676302708

[35]

Good Trans. Faraday Soc. (1967) 10.1039/tf9676302720

[36]

Benson Chem. Rev. (1978) 10.1021/cr60311a003

[37]

Bertrand Org. Prep. Proced. Int. (1994) 10.1080/00304949409458426

[38]

J. Texter , Reactions and Synthesis in Surfactant Systems , Marcel Dekker , New York , 2001 10.1201/9780203908662

[39]

Smook Ind. Eng. Chem. (1953) 10.1021/ie50528a050

[40]

Meerwein Chem. Ber. (1957) 10.1002/cber.19570900602

[41]

Hogan Org. Process Res. Dev. (2009) 10.1021/op9000862

[42]

Barton Tetrahedron (1988) 10.1016/s0040-4020(01)85895-6

[43]

Wilson J. Am. Chem. Soc. (1974) 10.1021/ja00830a030

[44]

Malet-Sanz Org. Biomol. Chem. (2010) 10.1039/c0ob00450b

[45]

Zheng Angew. Chem., Int. Ed. (2014) 10.1002/anie.201309851

[46]

Zheng Chem. Commun. (2014) 10.1039/c4cc03032j

[47]

An Chem. Commun. (2014) 10.1039/c4cc05401f

[48]

Luo Chem. Commun. (2015) 10.1039/c4cc07938h

[49]

Sheng Org. Chem. Front. (2017) 10.1039/c6qo00530f

[50]

Zheng Org. Biomol. Chem. (2015) 10.1039/c5ob01765c

Showing 50 of 109 references

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Metrics

341

Citations

109

References

Details

Published: Jan 01, 2018
Vol/Issue: 5(4)
Pages: 691-705
License: View

Authors

G

Guanyinsheng Qiu

College of Biological; Chemical Science and Engineering; Jiaxing University; Jiaxing 314001; China

K

Kaida Zhou

Department of Chemistry; Fudan University; Shanghai 200433; China

L

Liang Gao

Department of Natural Science and Computer Science; Ganzhou Teacher's College; Ganzhou; China

J

Jie Wu

Department of Chemistry; Fudan University; Shanghai 200433; China

Funding

National Natural Science Foundation of China Award: 21502069 and 21772067

Cite This Article

Guanyinsheng Qiu, Kaida Zhou, Liang Gao, et al. (2018). Insertion of sulfur dioxide via a radical process: an efficient route to sulfonyl compounds. Organic Chemistry Frontiers, 5(4), 691-705. https://doi.org/10.1039/c7qo01073g

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

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