- Synthesis of novel carbohydrate-based valine-derived formamide organocatalysts by CuAAC click chemistry and their application in asymmetric reduction of imines with trichlorosilane
-
Novel organocatalysts combining carbohydrate and N-formyl-l-valine derivatives were prepared by CuII-catalyzed diazo transfer and CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition CuAAC click chemistry. It was found that the carbohydrate-based valine-derived formamide organocatalyst had high catalytic activity for the asymmetric reduction of imines with trichlorosilane. The reduction can proceed at room temperature in toluene in high yield (up to 98%) and with excellent enantioselectivity (up to 94%). 'CuAAC' click chemistry is a bridge to link N-formyl-l-valine derived organocatalysts with carbohydrates.
- Ge, Xin,Qian, Chao,Chen, Xinzhi
-
-
Read Online
- Iron-catalyzed reductive coupling of nitroarenes with olefins: Intermediate of iron-nitroso complex
-
Using a single half-sandwich iron(II) compound, CpFe(1,2-Ph2PC6H4S)(NCMe) (Cp- = C5Me5-, 1) as a catalyst, reductive coupling of nitroarenes with olefins has been achieved by a well-defined iron(II)/(EtO)3SiH system. Through either inter- or intramolecular reductive coupling, various branched amines and indole derivatives have been directly synthesized in one-pot. Mechanistic studies showed that the catalysis is initiated by activation of nitroarenes by the iron(II) catalyst with silane, generating iron-nitrosoarene intermediate for the C-N bond coupling.
- Song, Heng,Yang, Zhuoyi,Tung, Chen-Ho,Wang, Wenguang
-
p. 276 - 281
(2019/12/24)
-
- Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe3O4
-
Magnetic nano-Fe3O4-supported organocatalysts were synthesized by anchoring valine-derived formamide onto the surface of Fe3O4 magnetic nanoparticles, which were applied in the asymmetric reduction of imines wit
- Ge, Xin,Qian, Chao,Ye, Xiaoming,Chen, Xinzhi
-
p. 65402 - 65407
(2015/08/18)
-
- Zirconium complexes stabilized by amine-bridged bis(phenolato) ligands as precatalysts for intermolecular hydroamination reactions
-
A series of zirconium complexes bearing amine-bridged bis(phenolato) ligands of different steric and electronic properties have been synthesized, and their activities in catalyzing intermolecular hydroamination reactions have been studied and compared. In
- Sun, Qiu,Wang, Yaorong,Yuan, Dan,Yao, Yingming,Shen, Qi
-
p. 20352 - 20360
(2015/12/04)
-
- Novel carbohydrate-derived pyridinecarboxylic organocatalysts for the enantioselective reduction of imines with trichlorosilane
-
A new type of carbohydrate-derived pyridinecarboxylic organocatalyst was prepared by fine-tuning a d-glucosamine backbone at the C-2 and C-3 positions. The carbohydrate-derived pyridinecarboxylic organocatalyst was used for the enantioselective reduction of imines with trichlorosilane. The reduction proceeded in high yield (up to 93%) and with moderate enantioselectivity (up to 75%).
- Ge, Xin,Qian, Chao,Chen, Yunbin,Chen, Xinzhi
-
p. 596 - 601
(2014/05/20)
-
- Synthesis of group 4 metal complexes stabilized by an amine-bridged bis(phenolato) ligand and their catalytic behavior in intermolecular hydroamination reactions
-
Zirconium and titanium complexes 1 and 2, bearing an amine-bridged bis(phenolato) ligand, have been synthesized and characterized. Although 1 and 2 were inactive in catalyzing intermolecular hydroamination reactions, cationic complexes generated in situ f
- Sun, Qiu,Wang, Yaorong,Yuan, Dan,Yao, Yingming,Shen, Qi
-
p. 994 - 1001
(2014/03/21)
-
- Indium-catalyzed hydroamination/hydrosilylation of terminal alkynes and aromatic amines through a one-pot, two-step protocol
-
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.
- Sakai, Norio,Takahashi, Nobuaki,Ogiwara, Yohei
-
supporting information
p. 5078 - 5082
(2014/08/18)
-
- Simple, efficient and reusable Pd-NHC catalysts for hydroamination
-
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
- Chen, Qian,Lv, Lanlan,Yu, Meng,Shi, Yanhui,Li, Yuling,Pang, Guangsheng,Cao, Changsheng
-
p. 18359 - 18366
(2013/10/21)
-
- Solvent- and catalyst-free direct reductive amination of aldehydes and ketones with Hantzsch ester: Synthesis of secondary and tertiary amines
-
A facile and rapid method for the parallel synthesis of a series of secondary and tertiary amines by the direct reductive amination of aldehydes and ketones with Hantzsch ester under solvent- and catalyst-free has been developed. The scope and limitation of this method are described.
- Nguyen, Quynh Pham Bao,Kim, Taek Hyeon
-
p. 4938 - 4943
(2013/07/25)
-
- Gallium trichloride catalyzed hydroamination of alkynes: Scope, limitation, and mechanistic studies by dft
-
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
- Li, Lei,Huang, Genping,Chen, Zhou,Liu, Wei,Wang, Xiufang,Chen, Yanmei,Yang, Lijuan,Li, Wu,Li, Yahong
-
supporting information
p. 5564 - 5572
(2012/11/07)
-
- S-benzyl isothiouronium chloride as a recoverable organocatalyst for the direct reductive amination of ketones with Hantzsch ester
-
The direct reductive amination of ketones using the Hantzsch ester in the presence of S-benzyl isothiouronium chloride as a recoverable organocatalyst is reported. A wide range of ketones as well as amines were found to give the expected products in moder
- Nguyen, Quynh Pham Bao,Kim, Taek Hyeon
-
experimental part
p. 1977 - 1982
(2012/08/07)
-
- Antioxidant for polyester fluids - alpha - methyl - n phenylbenzenemethanamine
-
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
- -
-
-