Recent Progress on the Zweifel Olefination: An Update

Xin Li; Qiuling Song

doi:10.1055/a-2172-1386

Synthesis, Table of Contents

Synthesis 2024; 56(13): 1979-1988
DOI: 10.1055/a-2172-1386

short review

Recent Progress on the Zweifel Olefination: An Update

Xin Li

^aInstitute of Next Generation Matter Transformation, College of Materials Science & Engineering, Huaqiao University, 668 Jimei Blvd, Xiamen 361021, Fujian, P. R. of China

,

Qiuling Song∗

^bKey Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou 350108, Fujian, P. R. of China

› Author Affiliations

Abstract

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Abstract

Over the past several decades, the Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, avoids the use of transition metals, and typically affords perfect stereospecificity, making it superior to many other olefination methods. Since Aggarwal’s summary of the 50-year history of the Zweifel olefination in 2017, remarkable achievements have been made in terms of employing new organometallic species, performing reactions through electrochemical or photochemical pathways, and developing methods that furnish new types of products. This short review summarizes and discusses the very recent progress made on the Zweifel olefination and its latest applications in the synthesis of natural products.

1 Introduction

2 Zweifel Olefination with New Organometallic Species

3 Zweifel Olefination with New Migrating Groups

4 Electrochemical and Photocatalyzed Zweifel Olefinations

5 New Elimination and Migration Patterns Involving the Zweifel Olefination

6 Zweifel Olefination in Natural Product Synthesis

7 Other Reactions Involving the Zweifel Olefination Mechanism

8 Conclusions and Outlook

Key words

Zweifel olefination - 1,2-migration - tetracoordinate - alkenyl boron - transition-metal-free - stereospecific

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References

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