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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 
a   School 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  ∗
b   Discovery Chemistry, Genomics Institute of the Novartis Research Foundation, San Diego, CA 92121, USA   Email: yliu2@gnf.org
,
Xuebin Liao  ∗
a   School 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
› Author AffiliationsThis work was supported by the Collaborative Innovation Center for Diagnosis and Treatment of Infectious Disease, Tsinghua-Peking Centre for Life Science.
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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


Publication History

Received: 24 June 2020

Accepted after revision: 04 August 2020

Article published online:
01 October 2020

© 2020. Thieme. All rights reserved

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