4058-17-7Relevant articles and documents
Organic Superbase t-Bu-P4 Catalyzes Amination of Methoxy(hetero)arenes
Shigeno, Masanori,Hayashi, Kazutoshi,Nozawa-Kumada, Kanako,Kondo, Yoshinori
supporting information, p. 5505 - 5508 (2019/08/01)
We report that the organic superbase t-Bu-P4 efficiently catalyzes the amination of methoxy(hetero)arenes with amine nucleophiles such as aniline, indoline, and aminopyridine derivatives. This catalytic reaction is effective for the transformation of elec
Ni(i)-Ni(iii) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(i) complexes
Inatomi, Takahiro,Fukahori, Yukino,Yamada, Yuji,Ishikawa, Ryuta,Kanegawa, Shinji,Koga, Yuji,Matsubara, Kouki
, p. 1784 - 1793 (2019/04/29)
Intermediate amide complexes of NHC-ligated monovalent nickel in Buchwald-Hartwig amination of aryl halides were isolated and structurally characterized. The amide complexes reacted with aryl bromide to form a cross-coupling product. Lowerature observation of the oxidative addition product of the Ni(i) amide complex with aryl bromide indicated the presence of a Ni(iii) intermediate. The results showed that a well-defined mononuclear NHC-Ni(i) complex can act as a key intermediate in homogeneous catalysis.
A General Palladium–Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
Choy, Pui Ying,Chung, Kin Ho,Yang, Qingjing,So, Chau Ming,Sun, Raymond Wai-Yin,Kwong, Fuk Yee
supporting information, p. 2465 - 2474 (2018/09/10)
The scope and limitations of the monoselective N-arylation of various amines by using aryl and hetaryl tosylates are presented. The air-stable and easily accessible Pd(OAc)2/CM-phos {CM-phos=2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1H-indole}catalyst system was able to deal with a wide range of aryl tosylate substrates as well as amine nucleophiles, including primary and secondary cyclic/acyclic aliphatic amines and anilines. NH-Bearing heterocycles such as indole, carbazole, pyrrole, 10-phenothiazine, and 10-phenoxazine were shown to be feasible coupling partners under this catalytic system. The described reaction conditions tolerate a wide range of functional groups and allow an array of aromatic amines as well as unsymmetrical amine products to be easily accessed from the various phenolic derivatives. Interestingly, this catalyst system even offers the opportunity to perform the reaction in water medium. We also report the intermolecular coupling of optically active α-central chiral amines with aryl tosylates without erosion of the enantiomeric purity.