Photoredox-Catalyzed Tandem Insertion/Cyclization Reactions of Difluoromethyl and 1,1-Difluoroalkyl Radicals with Biphenyl Isocyanides

Organic Letters
Zuxiao ZhangWilliam R Dolbier

Abstract

Using visible-light photoredox conditions, difluoromethylation and 1,1-difluoroalkylation of biphenyl isocyanides have allowed the synthesis of a series of 6-(difluoromethyl)- and 6-(1,1-difluoroalkyl)phenanthridines via tandem addition/cyclization/oxidation processes. The reactions are carried out in wet dioxane at room temperature using fac-Ir(ppy)3 as catalyst to form a large variety of substituted phenanthridine products in good to excellent yield.

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Citations

Feb 11, 2016·Organic Letters·Liubov I PanferovaAlexander D Dilman
Apr 9, 2016·Organic & Biomolecular Chemistry·Michael Gurry, Fawaz Aldabbagh
Apr 8, 2017·The Journal of Organic Chemistry·Honggui Huang, Yi Li
Nov 22, 2016·Chemical Society Reviews·Bingrui Song, Bin Xu
Feb 13, 2016·Organic & Biomolecular Chemistry·Jian LeiQiang Zhu
Apr 9, 2016·Chemical Communications : Chem Comm·Ye-bin WuChun Cai
Sep 22, 2018·Organic & Biomolecular Chemistry·Ailada CharoenpolChutima Kuhakarn
Jan 27, 2019·ChemSusChem·He-Huan XuHai-Chao Xu
Jan 8, 2020·Organic & Biomolecular Chemistry·Xiaojuan XieWen Wan
Jul 9, 2020·Organic & Biomolecular Chemistry·Hai-Tao TangYing-Ming Pan

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