139905-65-0Relevant articles and documents
Synthesis of sterically congested triarylamines by palladium-catalyzed amination
Riedmueller, Stefan,Kaufhold, Oliver,Spreitzer, Hubert,Nachtsheim, Boris J.
supporting information, p. 1391 - 1394 (2014/03/21)
An efficient protocol for the palladium-catalyzed synthesis of sterically congested triarylamines from commercially available 1-chloro- or 1-bromonaphthalenes and diarylamines is described. The application of alkyllithium reagents as strong bases and a combination of Pd(OAc)2 and SPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) plays a crucial role in the success of this otherwise difficult to achieve C-N coupling reaction. A variety of secondary aromatic amines with versatile steric and electronic properties can be successfully used in this transformation to give the desired triarylamines in up to 99 % yield. The obtained products are important structural motifs in hole-transport materials for organic light-emitting diode applications. A variety of secondary aromatic amines are coupled with 1-halonaphthalenes to give sterically highly congested triarylamines in up to 99 % yield. The key to the success of this transformation is prior deprotonation of the amine with strong bases such as n-hexyllithium. Copyright
Nickel-catalyzed triarylamine synthesis: Synthetic and mechanistic aspects
Li, Xin-Le,Wu, Wei,Fan, Xin-Heng,Yang, Lian-Ming
supporting information, p. 1232 - 1236 (2014/03/21)
An improved protocol was described for the amination of chloroarenes with diarylamines under NiCl2(PCy3)2 catalysis in the presence of a Grignard reagent as base. This method fully suits bromo-/iodoarene substrates as well, and even is expanded to certain aryl tosylates. A preliminary investigation into the mechanism suggests that this amination reaction might proceed through NiI and NiIII intermediates rather than via the usually expected Ni0-Ni II cycle.
