Issue 10, 2016

Visible light-mediated intramolecular C–H arylation of diazonium salts of N-(2-aminoaryl)benzoimines: a facile synthesis of 6-arylphenanthridines

Abstract

Utilizing [Ru(bpy)3]Cl2 as a photoredox catalyst and a blue LED as an irradiation source, moderate to good yields of 6-arylphenanthridines were obtained from aryl diazonium salts in situ formed from the reactions of N-(2-aminoaryl)benzoimines and tert-butyl nitrite (tBuONO). Although few visible light-mediated protocols are available for the synthesis of 6-arylphenanthridines, this work provides a new method to access them readily from inexpensive and environmentally benign starting materials.

Graphical abstract: Visible light-mediated intramolecular C–H arylation of diazonium salts of N-(2-aminoaryl)benzoimines: a facile synthesis of 6-arylphenanthridines

Supplementary files

Article information

Article type
Research Article
Submitted
17 Jun 2016
Accepted
02 Aug 2016
First published
02 Aug 2016

Org. Chem. Front., 2016,3, 1265-1270

Visible light-mediated intramolecular C–H arylation of diazonium salts of N-(2-aminoaryl)benzoimines: a facile synthesis of 6-arylphenanthridines

P. Natarajan, N. Kumar and M. Sharma, Org. Chem. Front., 2016, 3, 1265 DOI: 10.1039/C6QO00275G

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