881846-78-2Relevant articles and documents
Chiral Arylated Amines via C?N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
Cao, Rui,Li, Jing-Sheng,Song, Geyang,Tang, Wei-Jun,Wang, Chao,Xiao, Jianliang,Xue, Dong,Yang, Liu,Zhang, Wei
supporting information, p. 21536 - 21542 (2021/08/23)
The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.
Indium-catalyzed hydroamination/hydrosilylation of terminal alkynes and aromatic amines through a one-pot, two-step protocol
Sakai, Norio,Takahashi, Nobuaki,Ogiwara, Yohei
supporting information, p. 5078 - 5082 (2014/08/18)
We demonstrated that indium tribromide effectively functioned as a single catalyst for two successive steps in a one-pot procedure. First, the hydroamination of alkynes with anilines took place to give the Markovnikov product. Then, hydrosilylation of the imine intermediates by treatment with a hydrosilane substrate afforded the corresponding secondary amines.
Silver-catalyzed alkyne activation: The surprising ligand effect
Su, Yijin,Lu, Mei,Dong, Boliang,Chen, Hao,Shi, Xiaodong
supporting information, p. 692 - 696 (2014/04/03)
An unexpected ligand effect was discovered in the silver(I)-catalyzed alkyne activation. For both aldehyde-alkyne-amine (A3) condensation and intermolecular alkyne hydroamination, the type B complex (P:Ag=1:1) effectively promoted the reaction, while no reaction occurred with either no ligand or excess ligands under the identical conditions.
Simple, efficient and reusable Pd-NHC catalysts for hydroamination
Chen, Qian,Lv, Lanlan,Yu, Meng,Shi, Yanhui,Li, Yuling,Pang, Guangsheng,Cao, Changsheng
, p. 18359 - 18366 (2013/10/21)
A series of chelating NHC-palladium complexes with different alkane-bridges of the type Pd[NHC-(CH2)n-NHC]X2 (X = Br or Cl, n = 2-4) were synthesized, where NHC is a triazolyl-N-heterocyclic carbene donor ligand. The bromi
Gallium trichloride catalyzed hydroamination of alkynes: Scope, limitation, and mechanistic studies by dft
Li, Lei,Huang, Genping,Chen, Zhou,Liu, Wei,Wang, Xiufang,Chen, Yanmei,Yang, Lijuan,Li, Wu,Li, Yahong
, p. 5564 - 5572 (2012/11/07)
The successful application of gallium trichloride as a catalyst for the intermolecular hydroamination of alkynes with aromatic amines is reported. The reaction is effective with many aniline derivatives and shows exclusive selectivity for the Markovnikov
Triazole-Au(I) complexes: A new class of catalysts with improved thermal stability and reactivity for intermolecular alkyne hydroamination
Duan, Haifeng,Sengupta, Sujata,Petersen, Jeffrey L.,Akhmedov, Novruz G.,Shi, Xiaodong
supporting information; experimental part, p. 12100 - 12102 (2009/12/30)
(Chemical Equation Presented) A series of 1,2,3-triazole-bound cationic Au(I) catalysts have been synthesized, and their structures have been characterized by X-ray crystallography. Variable-temperature NMR studies revealed dynamic triazole-Au cation coor
A highly enantioselective Lewis basic organocatalyst for reduction of N-aryl imines with unprecedented substrate spectrum
Wang, Zhouyu,Ye, Xiaoxia,Wei, Siyu,Wu, Pengcheng,Zhang, Anjiang,Sun, Jian
, p. 999 - 1001 (2007/10/03)
L-Pipecolinic acid derived formamides have been developed as highly efficient and enantioselective Lewis basic organocatalysts for the reduction of N-aryl imines with trichlorosilane. Catalyst 4b afforded high isolated yields (up to 98%) and enantioselect
Decomplexation of (η-Arene)(η-cyclopentadienyl)iron(II) Hexafluorophosphates: a Convenient One-pot Arylation Procedure
Brown, Richard A.,Fernando, Sharon I. S.,Roberts, Roger M. G.
, p. 197 - 202 (2007/10/02)
A study has been made of the relative merits of range of decomplexation reagents in the demetallation of salts. 1,8-Phenanthroline have good yields of the free ligand when simple arene complexes were used but did not demetallate more sterically hindered species.The reaction was found to be light sensitive.Bipyridine gave much lower yields.Potassium tert-butoxide in pyridine or DMSO was found to be an excellent demetallating agent even with sterically crowded complexes.A one-pot arylation procedure was developed and extended to include a number of important heterocyclic derivatives.The mechanism of these decomplexation reactions is briefly adressesd.
Antioxidant for polyester fluids - alpha - methyl - n phenylbenzenemethanamine
-
, (2008/06/13)
An antioxidant for lubricating oils comprising an amine compound selected from substituted benzylamines or a substituted 1-amino-1,2,3,4-tetrahydro-naphthalene. The preferred anti-oxidants are N-(alpha -methyl -p -octylbenzyl) aniline, N-(alpha-methylbenz