Nickel-Catalyzed Intramolecular Desulfitative CN Coupling: A Synthesis of Aromatic Amines

Nickel-Catalyzed Intramolecular Desulfitative CN Coupling: A Synthesis of Aromatic Amines

A nickel-catalyzed intramolecular CN coupling reaction via SO2 extrusion is presented. The use of a catalytic amount of BPh3 allows the transformation to take place under much milder conditions (60 °C) than previously reported CN coupling reactions by CO or CO2 extrusion (160–180 °C). In addition,...

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Veröffentlicht in:Journal of organic chemistry 2020-04, Vol.85 (8), p.5702-5711
Hauptverfasser: Liu, Jiangjun, Jia, Xiuwen, Chen, Xuemeng, Sun, Haotian, Li, Yue, Kramer, Søren, Lian, Zhong
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Zusammenfassung:A nickel-catalyzed intramolecular CN coupling reaction via SO2 extrusion is presented. The use of a catalytic amount of BPh3 allows the transformation to take place under much milder conditions (60 °C) than previously reported CN coupling reactions by CO or CO2 extrusion (160–180 °C). In addition, this method displays good functional group tolerance and versatility, as it can be applied to the synthesis of dialkyl aryl amines, alkyl diaryl amines, and triaryl amines. The robustness of the desulfitative CN coupling is demonstrated by three high-yielding gram-scale reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00009