Rhodium-Catalyzed Directed C–H Cyanation of Arenes with N-Cyano‑N‑phenyl‑p‑toluenesulfonamide

Rhodium-Catalyzed Directed C–H Cyanation of Arenes with N-Cyano‑N‑phenyl‑p‑toluenesulfonamide

A Rh-catalyzed directed C–H cyanation reaction was developed for the first time as a practical method for the synthesis of aromatic nitriles. N-Cyano-N-phenyl-p-toluenesulfonamide, a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this...

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Veröffentlicht in:Journal of the American Chemical Society 2013-07, Vol.135 (29), p.10630-10633
Hauptverfasser: Gong, Tian-Jun, Xiao, Bin, Cheng, Wan-Min, Su, Wei, Xu, Jun, Liu, Zhao-Jing, Liu, Lei, Fu, Yao
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyanides - chemistry
Hydrocarbons, Aromatic - chemical synthesis
Methacrylates - chemistry
Models, Molecular
Nitriles - chemical synthesis
Organophosphorus Compounds - chemistry
Rhodium - chemistry
Sulfonamides - chemistry
Toluene - analogs & derivatives
Toluene - chemistry
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Zusammenfassung:A Rh-catalyzed directed C–H cyanation reaction was developed for the first time as a practical method for the synthesis of aromatic nitriles. N-Cyano-N-phenyl-p-toluenesulfonamide, a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this C–H cyanation process, and the reaction tolerates a variety of synthetically important functional groups.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja405742y