82749-62-0Relevant articles and documents
Palladium-Catalyzed Amination of Aryl Bromides: Use of Phosphinoether Ligands for the Efficient Coupling of Acyclic Secondary Amines
Marcoux, Jean-Francois,Wagaw, Seble,Buchwald, Stephen L.
, p. 1568 - 1569 (1997)
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Product selective reaction controlled by the combination of palladium nanoparticles, continuous microwave irradiation, and a co-existing solid; ligand-free Buchwald-Hartwig aminationvs.aryne amination
Akiyama, Toshiki,Arai, Masayoshi,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Murai, Kenichi,Murakami, Yosuke,Ohki, Yuuta,Ohta, Ryousuke,Sako, Makoto,Sirimangkalakitti, Natchanun,Suzuki, Takeyuki,Takahashi, Naoyuki,Takehara, Tsunayoshi,Yamada, Makito
supporting information, p. 8131 - 8137 (2021/10/29)
We have developed a continuous microwave irradiation-assisted Buchwald-Hartwig amination using our original Pd nanoparticle catalyst with a copper plate as a co-existing metal solid. In this methodology, a microwave-controlled product selectivity was achieved between Buchwald-Hartwig amination and aryne amination performed under strongly basic conditions and at a high reaction temperature, because a polar chemical species such as Ar-Pd-halogen might be activated selectively by microwave radiation. Moreover, our catalyst could be used repeatedly over 10 times, and the amount of Pd leaching could be suppressed to a low level.
An Effective Heterogeneous Copper Catalyst System for C-N Coupling and Its Application in the Preparation of 2-Methyl-4-methoxydiphenylamine (MMDPA)
Yi, Zhou,Huang, Manna,Wan, Yiqian,Zhu, Xinhai
, p. 3911 - 3920 (2018/09/29)
A ligand-recyclable, environmentally benign heterogeneous catalyst system composed of CuI and polystyrene-supported N (-(4-(aminomethyl)naphthalen-1-yl)- N (-phenyl-1 H -pyrrole-2-carbohydrazide (PSAP) has been established for Ullmann type C-N coupling based on the homogeneous catalyst system N ′, N ′-diphenyl-1 H -pyrrole-2-carbohydrazide/CuI. This heterogeneous catalyst system maintained the catalytic effectiveness of the homogeneous catalyst. A variety of functionalized aryl bromides can be efficiently aminated with aryl amines and aliphatic amines with high selectivity for amines over alcohols. Moreover, a practical application of this catalyst system to promote the reaction of commercially available 4-methoxy-2-methylaniline and bromobenzene in 10 mmol scale, provided 2-methyl-4-methoxydiphenylamine (MMDPA) with 93% yield with the merit of the approach being simple operation for work-up and purification.