Catalytic Metal-enabled Story Of Isocyanides For Use As “C1N1 ...

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Organic Chemistry Frontiers

Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry

Dianpeng Chen, *a Jianming Li,a Xin Wang,a Yingying Shan,a Keke Huang,b Xiaoyang Yan*c and Guanyinsheng Qiu *b Author affiliations

* Corresponding authors

a Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China E-mail: [email protected], [email protected]

b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China E-mail: [email protected]

c Jiaxing Hospital of T. C. M. ICU, Jiaxing, Zhejiang, China

Abstract

Cyclization reactions have attracted considerable attention in organic synthesis with regard to high atom economy and synthetic efficiency towards cyclic architectures. In particular, isocyanide-based cyclization has proven to be versatile for producing N-containing heterocycles among these cyclization processes. Until now, two typical modes of isocyanide-based cyclizations have been established, including the use of isocyanides as C1 synthons and C1N1 synthons. As we know, a series of reviews has documented advances in the use of isocyanides as C1 synthons. However, a critical and specific review with deep insights into isocyanide “C1N1” chemistry remains unexplored. Therefore, we would like to summarize recent advances in the use of isocyanides as “C1N1” synthons. To the best of our knowledge, a series of dual-functionalized isocyanides, such as 2-arylphenylisocyanides and 2-alkynylphenylisocyanides, has been efficiently realised by a model of radical chemistry, and these advances are not included in this manuscript since many elegant reviews have been published. To better illustrate the topic, this review is mainly organized according to various metal catalysts.

• This article is part of the themed collection: 2022 Organic Chemistry Frontiers Review-type Articles

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Article information

DOI https://doi.org/10.1039/D2QO00753C Article type Review Article Submitted 11 May 2022 Accepted 16 Jun 2022 First published 17 Jun 2022

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Org. Chem. Front., 2022,9, 4209-4220 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS

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Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry

D. Chen, J. Li, X. Wang, Y. Shan, K. Huang, X. Yan and G. Qiu, Org. Chem. Front., 2022, 9, 4209 DOI: 10.1039/D2QO00753C

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Dianpeng Chen Jianming Li Xin Wang Yingying Shan Keke Huang Xiaoyang Yan Guanyinsheng Qiu

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