1,2-Bis(phenylsulfonyl)ethylene (BPSE): A Potent Radical C2 Synthon Available in the Radical and Electron-Transfer-Based Organic Synthesis

Shuhei Sumino; Ilhyong Ryu; Frédéric Robert; Yannick Landais

doi:10.1055/s-0043-1775374

Synthesis, Table of Contents

Synthesis 2024; 56(21): 3233-3246
DOI: 10.1055/s-0043-1775374

short review

Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)

1,2-Bis(phenylsulfonyl)ethylene (BPSE): A Potent Radical C2 Synthon Available in the Radical and Electron-Transfer-Based Organic Synthesis

Shuhei Sumino

^aResearch Division of Organic Materials, Osaka Research Institute of Industrial Science and Technology (ORIST), 1-6-50, Morinomiya, Osaka 536-8553, Japan

^bOrganization for Research Promotion, Osaka Metropolitan University (OMU), 599-8531 Sakai, Osaka, Japan

,

Ilhyong Ryu∗

^bOrganization for Research Promotion, Osaka Metropolitan University (OMU), 599-8531 Sakai, Osaka, Japan

^cDepartment of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu, 30010 Taiwan, Taiwan

,

Frédéric Robert

^dUniversity Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255, 33400 Talence, France

,

Yannick Landais ∗

^dUniversity Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255, 33400 Talence, France

› Author Affiliations

Abstract

All articles of this category

Abstract

In this Short Review, we discuss radical reactions using 1,2-bis(phenylsulfonyl)ethylene (BPSE), which has drawn significant attention as a versatile building block for (phenylsulfonyl)ethenylation. Regardless of its E or Z form, BPSE exhibits reliable reactivity towards the attack of alkyl and aryl radicals in order to function as a reliable radical C2 synthon.

1 Introduction

2 Use in Radical Chain Reactions

3 Use in Reactions Utilizing an Electron-Transfer Process

4 Use in Radical-Based C–H Alkenylation

5 Conclusion

Key words

1,2-bis(phenylsulfonyl)ethylene - radical C2 synthon - β-scission - phenylsulfonyl radical - radical alkenylation

Full Text

References

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