Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides

Ying-Ying Liu; Shao-Han Sun; Xiang-Ting Min; Boshun Wan; Qing-An Chen

doi:10.1055/a-1751-1929

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(11): 2561-2573
DOI: 10.1055/a-1751-1929

short review

Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides

Ying-Ying Liu

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China URL: http://www.lbcs.dicp.ac.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Shao-Han Sun

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China URL: http://www.lbcs.dicp.ac.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Xiang-Ting Min∗

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China URL: http://www.lbcs.dicp.ac.cn

,

Boshun Wan

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China URL: http://www.lbcs.dicp.ac.cn

,

Qing-An Chen ∗

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China URL: http://www.lbcs.dicp.ac.cn

› Institutsangaben

Abstract

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Abstract

Phthalimide derivatives are prevalent in a wide array of biologically important molecules, including drugs, fungicides, and anticancer molecules. Thus, catalytic methods that directly edit the phthalimide moiety, in particular, decarbonylation and derivatization, could be strategically valuable for the modification of existing phthalimide molecular scaffolds. In recent years, considerable efforts have been devoted to emulating the transition-metal-catalyzed phthalimide decarbonylative reaction. A set of elegant strategies, including decarbonylative addition reactions with alkynes, alkenes, and benzynes, decarbonylative polymerization, alkylation, arylation, and protodecarbonylation, have been demonstrated. This review aims to highlight these advances and discusses the mechanism issues, to further expand application and promote developments in this field.

1 Introduction

2 Decarbonylative Addition Reaction with Alkynes

3 Decarbonylative Addition Reaction with Alkenes

4 Decarbonylative Addition Reaction with Benzyne

5 Decarbonylative Polymerization

6 Decarbonylative Alkylation

7 Decarbonylative Arylation

8 Protodecarbonylation

9 Conclusion and Outlook

Key words

decarbonylation reactions - phthalimides - amides - C–N bond activation - isoquinolones - alkynes - alkenes

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Referenzen

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