Synthesis 2017; 49(24): 5263-5284
DOI: 10.1055/s-0036-1590935
review
© Georg Thieme Verlag Stuttgart · New York

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
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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
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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
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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
› Author Affiliations
We thank NSFC (grant no. 21402200, 21502191, 21672213), Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000), The 100 Talents Program, ‘The 1000 Youth Talents Program’ for financial support.
Further Information

Publication History

Received: 27 July 2017

Accepted after revision: 25 August 2017

Publication Date:
08 November 2017 (online)


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