Ruthenium Catalyzed N-Alkylation of Cyclic Amines with Primary Alcohols

被引：5

作者：

Savela, Risto ^{[1
]}

Vogt, Dieter ^{[2
]}

Leino, Reko ^{[1
]}

机构：

[1] Abo Akad Univ, Lab Mol Sci & Technol, Biskopsgatan 8, Turku 20500, Finland

[2] Tech Univ Dortmund, Dept Biochem & Chem Engn, Lab Ind Chem, Emil Figge Str 66, D-44227 Dortmund, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 20期

基金：

芬兰科学院;

关键词：

Homogeneous catalysis; Amination; Borrowing hydrogen; Cyclic amines; Ruthenium; BORROWING HYDROGEN; SELECTIVE MONOMETHYLATION; HETEROGENEOUS CATALYSTS; NITROGEN-HETEROCYCLES; EFFICIENT CATALYST; SECONDARY ALCOHOLS; ALPHA-ALKYLATION; DIRECT AMINATION; PINCER COMPLEX; METHANOL;

D O I：

10.1002/ejoc.202000167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A robust alcohol amination protocol using common saturated amines and primary alcohols as starting materials is described. The reactions are catalyzed by combination of dichloro(p-cymene)ruthenium(II) dimer precatalyst with triphenylphosphine ligand, with the excess alcohol substrate or toluene functioning as the solvent. The catalyst and ligand residues can be precipitated from the reaction media by addition of hexane or cold diethyl ether, followed by precipitation and isolation of the product as a hydrochloride salt.

引用

页码：3030 / 3040

页数：11

共 86 条

[1] Esters, Including Triglycerides, and Hydrogen as Feedstocks for the Ruthenium-Catalyzed Direct N-Alkylation of Amines [J].

Adam, Rosa ;

Cabrero-Antonino, Jose R. ;

Junge, Kathrin ;

Jackstell, Ralf ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11049-11053

[2]

[Anonymous], 2018, ANGEW CHEM-GER EDIT

[3]

[Anonymous], 2016, ANGEW CHEM

[4] The Catalytic Amination of Alcohols [J].

Baehn, Sebastian ;

Imm, Sebastian ;

Neubert, Lorenz ;

Zhang, Min ;

Neumann, Helfried ;

Beller, Matthias .

CHEMCATCHEM, 2011, 3 (12) :1853-1864

[5] Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents [J].

Bailey, Christopher L. ;

Joh, Alexander Y. ;

Hurley, Zefan Q. ;

Anderson, Christopher L. ;

Singaram, Bakthan .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09) :3619-3628

[6] Use of (Cyclopentadienone)iron Tricarbonyl Complexes for C-N Bond Formation Reactions between Amines and Alcohols [J].

Brown, Thomas J. ;

Cumbes, Madeleine ;

Diorazio, Louis J. ;

Clarkson, Guy J. ;

Wills, Martin .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) :10489-10503

[7]

Bruce W. F., 1966, US, Patent No. [3252976 (A), 3252976]

[8] A Base and Solvent-Free Ruthenium-Catalyzed Alkylation of Amines [J].

Celaje, Jeff Joseph A. ;

Zhang, Xingyue ;

Zhang, Forrest ;

Kam, Lisa ;

Herron, Jessica R. ;

Williams, Travis J. .

ACS CATALYSIS, 2017, 7 (02) :1136-1142

[9] Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents [J].

Chandrika, Nishad Thamban ;

Shrestha, Sanjib K. ;

Ngo, Huy X. ;

Tsodikov, Oleg V. ;

Howard, Kaitlind C. ;

Garneau-Tsodikova, Sylvie .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (01) :158-173

[10] Sustainable and Selective Monomethylation of Anilines by Methanol with Solid Molecular NHC-Ir Catalysts [J].

Chen, Jiangbo ;

Wu, Jiajie ;

Tu, Tao .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (12) :11744-11751

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