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

Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides

Ying-Ying Liu
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China   URL: http://www.lbcs.dicp.ac.cn
b   University of Chinese Academy of Sciences, Beijing, 100049, P. R. of China
,
Shao-Han Sun
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China   URL: http://www.lbcs.dicp.ac.cn
b   University of Chinese Academy of Sciences, Beijing, 100049, P. R. of China
,
Xiang-Ting Min∗
a   Dalian 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
a   Dalian 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  ∗
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, P. R. of China   URL: http://www.lbcs.dicp.ac.cn
› Author AffiliationsFinancial support from the National Natural Science Foundation of China (Grant Nos. 21971234, 21772194, and 21572225) is acknowledged.
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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


Publication History

Received: 28 December 2021

Accepted after revision: 26 January 2022

Accepted Manuscript online:
26 January 2022

Article published online:
17 March 2022

© 2022. Thieme. All rights reserved

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