Isocyanide insertion: de novo synthesis of trifluoromethylated phenanthridine derivatives.

@article{Cheng2013IsocyanideID,
  title={Isocyanide insertion: de novo synthesis of trifluoromethylated phenanthridine derivatives.},
  author={Yuanzheng Cheng and Heng Jiang and Yan Zhang and Shouyun Yu},
  journal={Organic letters},
  year={2013},
  volume={15 21},
  pages={
          5520-3
        }
}
A mechanistically new strategy has been described for the simple, practical, and environmentally friendly preparation of 6-(trifluoromethyl)phenanthridine derivatives using ionic isocyanide insertion from biphenyl isocyanide derivatives and Umemoto's reagent. These reactions were promoted only by inorganic base in good-to-excellent chemical yields without any external stoichiometric oxidants and radical initiators. 
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97 Citations

97 Citations

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Isocyanide Insertion: De novo Synthesis of Trifluoromethylated Phenanthridine Derivatives.
Ionic isocyanide insertion from biphenyl isocyanide derivative and Usemoto′s reagent (II) is developed resulting in an efficient synthesis of 6-trifluoromethyl substituted phenanthridines and a…
Microwave-Assisted Synthesis of Phenanthridines by Radical Insertion/Cyclization of Biphenyl Isocyanides.
A rapid microwave-assisted approach for the synthesis of phenanthridine derivatives from the radical insertion/cyclization reaction of biphenyl isocyanides with a C(sp(3))-H bond adjacent to a…
Palladium-Catalyzed Difluoroalkylation of Isocyanides: Access to Difluoroalkylated Phenanthridine Derivatives.
An efficient and general method for the synthesis of difluoroalkylated phenanthridine derivatives through palladium-catalyzed reaction of difluoroalkyl bromides with isocyanides is described. The…
Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides with diaryliodonium salts.
TLDR
The methodology presented here represents the first example of isoquinoline synthesis via somophilic isocyanide insertion, and it is claimed that this synthesis is the first of its kind.
Copper-catalyzed trifluoromethylalkynylation of isocyanides.
The title reaction proceeds with acetylenic triflones and isocyanides under mild conditions using copper as a catalyst. This transformation provides an efficient access to (E)-N-alkyl trifluoromethyl…
Synthesis of polysubstituted phenanthridines via ligand-free copper-catalyzed annulation.
A novel procedure for the cascade reaction of the addition of a Grignard reagent to a nitrile with a copper-catalyzed C-N bond coupling was developed, which afforded various polysubstituted…
Synthesis of 6-carboxylated phenanthridines by oxidative alkoxycarbonylation–cyclization of 2-isocyanobiphenyls with carbazates
Manganese(II)-catalyzed modular synthesis of isoquinolines from vinyl isocyanides and hydrazines
An efficient manganese(II)-catalyzed oxidative radical cascade reaction was developed for the modular synthesis of multi-substituted isoquinolines from easily accessible vinyl isocyanides and…
Synthesis of 6-aminophenanthridines via palladium-catalyzed insertion of isocyanides into N-sulfonyl-2-aminobiaryls
A robust route to a diverse set of 6-aminophenanthridines via palladium-catalyzed C–H activation of N-sulfonyl-2-aminobiaryl and isocyanide insertion is reported. This transformation could also…
Synthesis of 6-(arylthio)phenanthridines by copper-catalyzed tandem reactions of 2-biaryl isothiocyanates with diaryliodonium salts.
TLDR
A novel copper-catalyzed tandem C-S/C-C bond-forming reaction of 2-biaryl isothiocyanates with diaryliodonium salts was developed and this methodology has been successfully applied to the synthesis of trisphaeridine.
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