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

Jiangjun Liu, Xiuwen Jia, Xuemeng Chen, Haotian Sun, Yue Li, Søren Kramer, Zhong Lian*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalJournal of organic chemistry
Volume85
Issue number8
Pages (from-to)5702-5711
ISSN0022-3263
DOIs
Publication statusPublished - 2020

Cite this