94026-73-0Relevant academic research and scientific papers
Synthesis of N-heterocyclic carbene-Pd(II) complexes and their catalytic activity in the Buchwald-Hartwig amination of aryl chlorides
Zhang, Zhi-Mao,Gao, Yu-Jue,Lu, Jian-Mei
, p. 7308 - 7314 (2017/12/01)
Novel N-heterocyclic carbene-palladium(II) complexes using 2-picolinic acid as the ancillary ligand have been successfully developed under mild conditions. Their catalytic activity in organic synthesis has been initially tested in the Buchwald-Hartwig amination of secondary and primary amines with aryl chlorides. Various substituents on both substrates can be tolerated, giving the desired coupling products in good to almost quantitative yields. The minimum catalyst loading can be 0.01 mol%, implying their potential application toward industrial processes.
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
Copper-catalyzed N-arylation of amines with hypervalent iodonium salts
Kang, Suk-Ku,Lee, Sang-Ho,Lee, Duckhee
, p. 1022 - 1024 (2007/10/03)
The copper-catalyzed N-arylation of amines with hypervalent iodonium compounds with secondary aliphatic amines, aromatic amines, azoles and amides was accomplished with catalytic CuI (10 mol%) or Cu(acac)2 (5 mol%) in the presence of Na2CO3 or K2CO3 as a base in CH2Cl2 or toluene under mild conditions.
ALIPHATIC C-H, N-INSERTION VERSUS AROMATIC N-SUBSTITUTION IN THE REACTION OF ARYLNITRENIUM-BORON TRIFLUORIDE COMPLEXES WITH METHYLATED BENZENES
Spagnolo, Piero,Zanirato, Paolo
, p. 961 - 964 (2007/10/02)
The boron trifluoride promoted decomposition of a number of substituted phenyl azides in toluene, para-xylene, meta-xylene or mesitylene at 60 gradC, leads preferentially to N-benzylamines or diarylamines depending on both ring substituent effect and nucleophilic character of the solvent.
