Synthesis 2020; 52(02): 290-296
DOI: 10.1055/s-0039-1690218
paper
© Georg Thieme Verlag Stuttgart · New York

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

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
› Author Affiliations
This work is financially supported by the National Natural Science Foundation of China (No. 81102334, 31370372, 31170323), the Program for New Century Excellent Talents in University (State Education Ministry of China; NCET-2008-0224), and the Fundamental Research Funds for the Central Universities (2017KFYXJJ152).
Further Information

Publication History

Received: 27 August 2019

Accepted after revision: 02 October 2019

Publication Date:
05 November 2019 (online)


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.

Supporting Information