Synthesis 2014; 46(20): 2711-2726
DOI: 10.1055/s-0034-1379217
feature article
© Georg Thieme Verlag Stuttgart · New York

Somophilic Isocyanide Insertion: Synthesis of 6-Arylated and 6-Trifluoro­methylated Phenanthridines

Ruzhi Wang
a  State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China   Fax: +86(25)83317761   Email: yushouyun@nju.edu.cn   Email: njuzy@nju.edu.cn
,
Heng Jiang
a  State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China   Fax: +86(25)83317761   Email: yushouyun@nju.edu.cn   Email: njuzy@nju.edu.cn
,
Yuanzheng Cheng
a  State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China   Fax: +86(25)83317761   Email: yushouyun@nju.edu.cn   Email: njuzy@nju.edu.cn
,
Adnan A. Kadi
b  Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
,
Hoong-Kun Fun
b  Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
c  X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
,
Yan Zhang*
a  State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China   Fax: +86(25)83317761   Email: yushouyun@nju.edu.cn   Email: njuzy@nju.edu.cn
b  Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
,
Shouyun Yu*
a  State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China   Fax: +86(25)83317761   Email: yushouyun@nju.edu.cn   Email: njuzy@nju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 28 July 2014

Accepted after revision: 05 September 2014

Publication Date:
30 September 2014 (online)


Abstract

A visible-light-promoted biaryl isocyanide insertion reaction has been developed to synthesize phenanthridine derivatives. The insertion proceeds via a radical process, and diaryliodonium salts and Umemoto’s reagent were used as radical sources. A variety of 6-arylated, as well as 6-trifluoromethylated, phenanthridine derivatives were obtained smoothly in good to excellent yields under mild conditions.

Supporting Information

 
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