Alkylation of cyclic amines with alcohols catalyzed by Ru(II) complexes bearing N-Heterocyclic carbenes

被引:12
作者
Ulu, Oznur Dogan [1 ]
Gurbuz, Nevin [1 ,2 ]
Ozdemir, Ismail [1 ,2 ]
机构
[1] Inonu Univ, Catalysis Res & Applicat Ctr, TR-44280 Malatya, Turkey
[2] Inonu Univ, Fac Sci & Arts, Dept Chem, TR-44280 Malatya, Turkey
关键词
N-Heterocyclic carbene; Ruthenium; Alkylation; Cyclic amine; TRANSFER HYDROGENATION; RUTHENIUM COMPLEXES; OLEFIN METATHESIS; BETA-ALKYLATION; SELECTIVE ALKYLATION; EFFICIENT CATALYSTS; AROMATIC AMINE; IRIDIUM; NHC; LIGAND;
D O I
10.1016/j.tet.2017.09.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper includes the synthesis of 2-(1,3-dioxane-2-yl)ethyl substituted benzimidazole substituted N-heterocyclic carbenes precursors and their ruthenium complexes. Synthesized compounds were characterized by elemental analysis and NMR spectroscopy. All complexes have been tested in the alkylation of pyrrolidine and morpholine with alcohols, showing an excellent activity in this reaction. (C) 2017 Published by Elsevier Ltd.
引用
收藏
页码:645 / 651
页数:7
相关论文
共 43 条
[1]   A Highly Active Bifunctional Iridium Complex with an Alcohol/Alkoxide-Tethered N-Heterocyclic Carbene for Alkylation of Amines with Alcohols [J].
Bartoszewicz, Agnieszka ;
Marcos, Rocio ;
Sahoo, Suman ;
Inge, A. Ken ;
Zou, Xiaodong ;
Martin-Matute, Belen .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (45) :14510-14519
[2]   Synthesis and catalytic properties of N-functionalized carbene complexes of rhodium(I) and ruthenium(II) [J].
Cetinkaya, B ;
Ozdemir, I ;
Dixneuf, PH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 534 (1-2) :153-158
[3]   Ruthenium-carbene catalysts for the synthesis of 2,3-dimethylfuran [J].
Cetinkaya, B ;
Ozdemir, I ;
Bruneau, C ;
Dixneuf, PH .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 118 (01) :L1-L4
[4]   Synthesis, characterization and catalytic activity of saturated and unsaturated N-heterocyclic carbene iridium(I) complexes [J].
Chang, Yung-Hung ;
Fu, Ching-Feng ;
Liu, Yi-Hong ;
Peng, Shei-Ming ;
Chen, Jwu-Ting ;
Liu, Shiuh-Tzung .
DALTON TRANSACTIONS, 2009, (05) :861-867
[5]   Indenylidene Ruthenium Complex Bearing a Sterically Demanding NHC Ligand: An Efficient Catalyst for Olefin Metathesis at Room Temperature [J].
Clavier, Herve ;
Urbina-Blanco, Cesar A. ;
Nolan, Steven P. .
ORGANOMETALLICS, 2009, 28 (09) :2848-2854
[6]  
Costa A. P., 2008, ORGANOMETALLICS, V27, P1305
[7]  
Costa AP, 2009, ORGANOMETALLICS, V27, P1305
[8]   Polypyrrole-functionalized ruthenium carbene catalysts as efficient heterogeneous systems for olefin epoxidation [J].
Dakkach, Mohamed ;
Fontrodona, Xavier ;
Parella, Teodor ;
Atlamsani, Ahmed ;
Romero, Isabel ;
Rodriguez, Montserrat .
DALTON TRANSACTIONS, 2014, 43 (26) :9916-9923
[9]   Synthesis and Small Molecule Reactivity of trans-Dihydride Isomers of Ru(NHC)2(PPh3)2H2 (NHC = N-Heterocyclic Carbene) [J].
Davies, Caroline J. E. ;
Lowe, John P. ;
Mahon, Mary F. ;
Poulten, Rebecca C. ;
Whittlesey, Michael K. .
ORGANOMETALLICS, 2013, 32 (17) :4927-4937
[10]   Synthesis and application of new N-heterocyclic carbene ruthenium complexes in catalysis:: A case study [J].
Delaude, L ;
Demonceau, A ;
Noels, AF .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (02) :203-215