Metal-Free Synthesis 6-Benzylphenanthridines via Radical Addition/Cyclization of 2-Isocyanobiphenyls

Yuling Lu; Li Chen; Xia Chen; Meng Yao; Zengwei Luo; Yonghui Zhang

doi:10.1055/s-0039-1690218

Synthesis, Table of Contents

Synthesis 2020; 52(02): 290-296
DOI: 10.1055/s-0039-1690218

paper

Metal-Free Synthesis 6-Benzylphenanthridines via Radical Addition/Cyclization of 2-Isocyanobiphenyls

Authors

Yuling Lu
Li Chen
Xia Chen
Meng Yao
Zengwei Luo∗

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. of China Email: luozengwei@hust.edu.cn Email: zhangyh@mails.tjmu.edu.cn
Yonghui Zhang∗

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. of China Email: luozengwei@hust.edu.cn Email: zhangyh@mails.tjmu.edu.cn

Abstract

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Abstract

A simple and practical approach has been established for the synthesis of 6-benzylphenanthridines from benzylic hydrocarbons and 2-isocyanobiphenyls via C(sp³)–H/C(sp²)–H bond functionalization under metal-free condition. The reaction exhibits good functional group tolerance and delivers the target products in moderate to excellent yields. The preliminary mechanistic investigation revealed that a radical intermediate might be involved in this reaction.

Key words

phenanthridine - metal-free - radical - isocyanobiphenyl - toluene

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References

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Supplementary Material

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