Recent Progress on Radical Decarboxylative Alkylation for Csp3–C Bond Formation

Yajun Li; Liang Ge; Munira Taj Muhammad; Hongli Bao

doi:10.1055/s-0036-1590935

Synthesis, Table of Contents

Synthesis 2017; 49(24): 5263-5284
DOI: 10.1055/s-0036-1590935

review

Recent Progress on Radical Decarboxylative Alkylation for Csp³–C Bond Formation

Yajun Li

Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

,

Liang Ge

Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

,

Munira Taj Muhammad

Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

,

Hongli Bao *

Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

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Abstract

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Abstract

Radical decarboxylation has emerged as an attractive method for the formation of C–C bonds starting from easily accessible carboxylic acids. In this review, we attempt to bring the readers up to date in this rapidly expanding field. Specifically, we will cover recent advances in Csp³–C bond formation via the radical decarboxylation of aliphatic carboxylic acids and their activated forms, such as N-hydroxyphthalimide esters (NHP esters), alkyl diacyl peroxides, alkyl peresters, and aryliodine(III) dicarboxylates. The scope and limitation of these transformations will be discussed, highlighting gaps in knowledge and research and examining the mechanisms underlying radical decarboxylation. We aim to make this review a stepping stone for further development in this field.

1 Introduction

2 Aliphatic Carboxylic Acids

3 N-Hydroxyphthalimide Esters (NHP Esters)

4 Alkyl Diacyl Peroxides

5 Alkyl Peresters

6 Aryliodine(III) Dicarboxylates

7 Conclusion

Key words

radical - carboxylic acids - decarboxylation - redox-active esters - C–C bond formation

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References

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