N-Propylphthalimide-Substituted Silver(I) N-Heterocyclic Carbene Complexes and Ruthenium(II) N-Heterocyclic Carbene Complexes: Synthesis and Transfer Hydrogenation of Ketones

被引:23
作者
Aktas, Aydin [1 ]
Gok, Yetkin [1 ]
机构
[1] Inonu Univ, Fac Arts & Sci, Dept Chem, TR-44280 Malatya, Turkey
关键词
N-heterocyclic carbenes; Silver and ruthenium complexes; Catalysis; Transfer hydrogenation; OLEFIN METATHESIS CATALYSTS; ORGANIC-SYNTHESIS; CYCLOPROPANATION; VINYLIDENES; LIGANDS;
D O I
10.1007/s10562-014-1453-8
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
This study deals with the synthesis of N-propylphthalimide substituted Ag(I)-N-heterocyclic carbene (NHC) complexes and N-propylphthalimide substituted Ru(II)-NHC complexes in the transfer hydrogenation of ketones. The Ag(I)-NHC complexes were synthesized from the imidazolium salts and Ag2O in dichloromethane at room temperature. The Ru(II)-NHC complexes have been prepared from Ag(I)-NHC complexes using transmetallation method. The six N-propylphthalimide substituted Ag(I)-NHC complexes and six N-propylphthalimide substituted Ru(II)-NHC complexes have been characterized by spectroscopic techniques and elemental analyses. N-propylphthalimide substituted Ru(II)-NHC complexes have been analyzed as catalysts for the transfer hydrogenation of ketones and exhibit activity in this reaction. This study deals with the synthesis of N-propylphthalimide substituted Ag(I)-N-heterocyclic carbene (NHC) complexes and N-propylphthalimide substituted Ru(II)-NHC complexes in the transfer hydrogenation of ketones. The Ag(I)-NHC complexes were synthesized from the imidazolium salts and Ag2O in dichloromethane at room temperature. The Ru(II)-NHC complexes have been prepared from Ag(I)-NHC complexes using transmetallation method. The six N-propylphthalimide substituted Ag(I)-NHC complexes and six N-propylphthalimide substituted Ru(II)-NHC complexeshavebeencharacterizedbyspectroscopictechniquesandelementalanalyses. N-propylphthalimide substituted Ru(II)-NHC complexes have been analyzed as catalysts for the transfer hydrogenation of ketones and exhibit activity in this reaction.
引用
收藏
页码:631 / 639
页数:9
相关论文
共 43 条
[1]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[2]   The quest for stable carbenes [J].
Arduengo, AJ ;
Krafczyk, R .
CHEMIE IN UNSERER ZEIT, 1998, 32 (01) :6-14
[3]   Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].
Austin, JF ;
Kim, SG ;
Sinz, CJ ;
Xiao, WJ ;
MacMillan, DWC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487
[4]   Metal vinylidenes in catalysis [J].
Bruneau, C ;
Dixneuf, PH .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) :311-323
[5]   Synthesis of functionalized olefins by cross and ring-closing metatheses [J].
Chatterjee, AK ;
Morgan, JP ;
Scholl, M ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784
[6]   Bis-N-heterocyclic carbene ruthenium(II) carbonyl complexes: Synthesis, structural characterization and catalytic activities in transfer hydrogenation of ketones [J].
Cheng, Yong ;
Lu, Xiang-Yong ;
Xu, Hui-Jun ;
Li, Yi-Zhi ;
Chen, Xue-Tai ;
Xue, Zi-Ling .
INORGANICA CHIMICA ACTA, 2010, 363 (02) :430-437
[7]   Synthesis, characterization, and application to transfer hydrogenation of η6-(3,4,5-trimethoxybenzyl)-η1-N-heterocyclic carbene-ruthenium complex [J].
Demir, Serpil ;
Ozdemir, Ismail ;
Cetinkaya, Bekir ;
Sahin, Ertan ;
Arici, Cengiz .
JOURNAL OF COORDINATION CHEMISTRY, 2011, 64 (14) :2565-2572
[8]   CYCLOPROPANATION OF ACTIVATED OLEFINS CATALYZED BY RU-PHOSPHINE COMPLEXES [J].
DEMONCEAU, A ;
DIAS, EA ;
LEMOINE, CA ;
STUMPF, AW ;
NOELS, AF ;
PIETRASZUK, C ;
GULINSKI, J ;
MARCINIEC, B .
TETRAHEDRON LETTERS, 1995, 36 (20) :3519-3522
[9]   Synthesis of chiral N-heterocyclic carbene (NHC) ligand precursors and formation of ruthenium(II) complexes for transfer hydrogenation catalysts [J].
DePasquale, Joseph ;
White, Nicholas J. ;
Ennis, Erin J. ;
Zeller, Matthias ;
Foley, Joe P. ;
Papish, Elizabeth T. .
POLYHEDRON, 2013, 58 :162-170
[10]   Ruthenium(II) N,S-heterocyclic carbene complexes and transfer hydrogenation of ketones [J].
Ding, Nini ;
Hor, T. S. Andy .
DALTON TRANSACTIONS, 2010, 39 (42) :10179-10185