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

Tiebo Xiao; Hongtai Huang; Devireddy Anand; Lei Zhou

doi:10.1055/s-0039-1690844

Synthesis, Table of Contents

Synthesis 2020; 52(11): 1585-1601
DOI: 10.1055/s-0039-1690844

review

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

Tiebo Xiao ∗

^aFaculty 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

^aFaculty 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

^bSchool of Chemistry, Sun Yat-sen University, 135 Xingang West Road, Guangzhou, 510275, P. R. of China Email: zhoul39@mail.sysu.edu.cn

,

Lei Zhou∗

^bSchool of Chemistry, Sun Yat-sen University, 135 Xingang West Road, Guangzhou, 510275, P. R. of China Email: zhoul39@mail.sysu.edu.cn

› Author Affiliations

Abstract

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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

Key words

iminyl radicals - C–C bond cleavage - cyanoalkylation - nitriles - single-electron transfer

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References

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