Recent Progress in Radical Decarboxylative Functionalizations Enabled by Transition-Metal (Ni, Cu, Fe, Co or Cr) Catalysis

Hui Chen; Yahu A Liu; Xuebin Liao

doi:10.1055/s-0040-1707273

Synthesis, Table of Contents

Synthesis 2021; 53(01): 1-29
DOI: 10.1055/s-0040-1707273

review

Recent Progress in Radical Decarboxylative Functionalizations Enabled by Transition-Metal (Ni, Cu, Fe, Co or Cr) Catalysis

Hui Chen

^aSchool of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Beijing Advanced Innovation Center for Structural Biology, Tsinghua University, Beijing 100084, P. R. of China Email: liaoxuebin@mail.tsinghua.edu.cn

,

Yahu A Liu ∗

^bDiscovery Chemistry, Genomics Institute of the Novartis Research Foundation, San Diego, CA 92121, USA Email: yliu2@gnf.org

,

Xuebin Liao ∗

^aSchool of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Beijing Advanced Innovation Center for Structural Biology, Tsinghua University, Beijing 100084, P. R. of China Email: liaoxuebin@mail.tsinghua.edu.cn

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Abstract

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Abstract

Aliphatic carboxylic acids are abundant in natural and synthetic sources and are widely used as connection points in many chemical transformations. Radical decarboxylative functionalization promoted by transition-metal catalysis has achieved great success, enabling carboxylic acids to be easily transformed into a wide variety of products. Herein, we highlight the recent advances made on transition-metal (Ni, Cu, Fe, Co or Cr) catalyzed C–X (X = C, N, H, O, B, or Si) bond formation as well as syntheses of ketones, amino acids, alcohols, ethers and difluoromethyl derivatives via radical decarboxylation of carboxylic acids or their derivatives, including, among others, redox-active esters (RAEs), anhydrides, and diacyl peroxides.

1 Introduction

2 Ni-Catalyzed Decarboxylative Functionalizations

3 Cu-Catalyzed Decarboxylative Functionalizations

4 Fe-Catalyzed Decarboxylative Functionalizations

5 Co- and Cr-Catalyzed Decarboxylative Functionalizations

6 Conclusions

Key words

carboxylic acids - decarboxylative functionalization - transition metals - radicals - redox-active esters (RAEs) - C–X bond formation - catalysis

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References

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