Synthesis 2020; 52(11): 1585-1601
DOI: 10.1055/s-0039-1690844
review
© Georg Thieme Verlag Stuttgart · New York

Iminyl-Radical-Triggered C–C Bond Cleavage of Cycloketone Oxime Derivatives: Generation of Distal Cyano-Substituted Alkyl Radicals and Their Functionalization

Tiebo Xiao
a  Faculty of Science, Kunming University of Science and Technology, 727 South Jingming Road, Chenggong District, Kunming, 650500, P. R. of China   Email: xiaotb@kust.edu.cn
,
Hongtai Huang
a  Faculty of Science, Kunming University of Science and Technology, 727 South Jingming Road, Chenggong District, Kunming, 650500, P. R. of China   Email: xiaotb@kust.edu.cn
,
Devireddy Anand
b  School of Chemistry, Sun Yat-sen University, 135 Xingang West Road, Guangzhou, 510275, P. R. of China   Email: zhoul39@mail.sysu.edu.cn
,
Lei Zhou
b  School of Chemistry, Sun Yat-sen University, 135 Xingang West Road, Guangzhou, 510275, P. R. of China   Email: zhoul39@mail.sysu.edu.cn
› Author Affiliations
We are grateful for funding from the National Key Basic Research Program For Youth, China (Grant No. 2016YFA0602900), the National Science Foundation (NSF) of Guangdong Province for Distinguished Young Scholars (Grant No. 2016A030306029) and the National Natural Science Foundation of China (NSFC, Grant No. 21871300). T.X. thanks the NSFC (Grant No. 21801101) for financial support.
Further Information

Publication History

Received: 02 December 2019

Accepted after revision: 07 February 2020

Publication Date:
05 March 2020 (online)


Abstract

Alkyl nitriles are versatile building blocks in organic synthesis because the cyano group can be easily converted into other functional groups. Iminyl-radical-triggered C–C bond cleavage of cycloketone oxime­ derivatives provides a practical route to access distal cyano-substituted alkyl radicals, which has given chemists a new radical reaction platform for the synthesis of diverse alkyl nitriles. This review provides an overview of various types of radical cyanoalkylation via ring opening of cycloketone oxime derivatives.

1 Introduction

2 C–C Bond Formation

2.1 Alkenes as Radical Acceptors

2.2 Aromatic Rings as Radical Acceptors

2.3 Organometallic Reagents as Radical Acceptors

2.4 Cyanoalkyl-Radical-Triggered Cyclization Reactions

2.5 Miscellaneous

3 C–Heteroatom Bond Formation

3.1 C–O Bond Formation

3.2 C–N Bond Formation

3.3 C–S Bond Formation

3.4 C–Halogen Bond Formation

3.5 C–B Bond Formation

4 Conclusion

 
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