Ruthenium(II) Picolyl-NHC Complexes: Synthesis, Characterization, and Catalytic Activity in Amine N-alkylation and Transfer Hydrogenation Reactions

被引:127
|
作者
Fernandez, Francys E. [1 ]
Carmen Puerta, M. [1 ]
Valerga, Pedro [1 ]
机构
[1] Univ Cadiz, Fac Ciencias, Dept Ciencia Mat & Ingn Met & Quim Inorgan, Cadiz 11510, Spain
关键词
HETEROCYCLIC-CARBENE COMPLEXES; C-H ACTIVATION; EFFICIENT CATALYSTS; NICKEL(II) COMPLEXES; POLYMERIZATION BEHAVIOR; RHODIUM(I) COMPLEXES; PALLADIUM COMPLEXES; BORROWING HYDROGEN; IRIDIUM COMPLEXES; RU(II) COMPLEXES;
D O I
10.1021/om300692a
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ruthenium(II) p-cymene complexes with picolyl-functionalized N-heterocyclic carbenes [(eta(6)-p-cymene)Ru(L)(Cl)]-[PF6] (L = 3-methyl-1-(2-picolyl)imidazol-2-ylidene (1a), 3-isopropyl-1-(2-picolyl)imidazol-2-ylidene (1b), 3,4,5-trimethyl-1-(2-picoly)imidazol-2-ylidene (1c), 3-mesityl-1-(2-picolyl)imidazol-2-ylidene (1d), 3-methyl-1-(2-picolyl)benzoimidazol-2-ylidene (1f), 3-methyl-1-(2-picolyl)-4,5-dichloroimidazol-2-ylidene (1f), 3-phenyl-1-(2-picolyl)imidazol-2-ylidene (1g)) have been synthesized and characterized. Compounds 1 a-g were recrystallized, and X-ray crystal structures are reported for 1a,f. Furthermore, compounds 1a-f show catalytic activity in transfer hydrogenation of ketones and N-alkylation of amines. Notably, complexes 1a,c,f were found to be very efficient and versatile catalysts toward transfer hydrogenation of a wide range of ketones and imines in addition to N-alkylation of several amines.
引用
收藏
页码:6868 / 6879
页数:12
相关论文
共 50 条
  • [31] Bis-N-heterocyclic carbene ruthenium(II) carbonyl complexes: Synthesis, structural characterization and catalytic activities in transfer hydrogenation of ketones
    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
  • [32] Synthesis of ruthenium N-heterocyclic carbene (NHC) complexes as catalysts for transfer hydrogenation of carbonyl compounds
    DePasquale, Joseph
    Kumar, Mukesh
    Zeller, Matthias
    Papish, Elizabeth T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [33] 3-Aminoquinazoline–phosphine ligands and their ruthenium(II) complexes: application in catalytic hydrogenation and transfer hydrogenation reactions
    Mustafa Kemal Yılmaz
    Mustafa Keleş
    Transition Metal Chemistry, 2018, 43 : 285 - 292
  • [34] 3-Aminoquinazoline-phosphine ligands and their ruthenium(II) complexes: application in catalytic hydrogenation and transfer hydrogenation reactions
    Yilmaz, Mustafa Kemal
    Keles, Mustafa
    TRANSITION METAL CHEMISTRY, 2018, 43 (03) : 285 - 292
  • [35] Synthesis, characterization and catalytic activity of nickel NHC complexes
    Wlodarska, Agata
    Golaszewska-Gajda, Jowita
    Dranka, Maciej
    Pietrzykowski, Antoni
    MOLECULAR CATALYSIS, 2017, 440 : 25 - 35
  • [36] Synthesis and catalytic activity of histidine-based NHC ruthenium complexes
    Monney, Angele
    Venkatachalam, Galmari
    Albrecht, Martin
    DALTON TRANSACTIONS, 2011, 40 (12) : 2716 - 2719
  • [37] Ruthenium Complexes Bearing α-Diimine Ligands and Their Catalytic Applications in N-Alkylation of Amines, α-Alkylation of Ketones, and β-Alkylation of Secondary Alcohols
    Gayathri, Sekar
    Viswanathamurthi, Periasamy
    Bertani, Roberta
    Sgarbossa, Paolo
    ACS OMEGA, 2022, : 33107 - 33122
  • [38] Synthesis, characterization, and application in asymmetric hydrogenation reactions of chiral ruthenium(II) diphosphine complexes
    Zanetti, NC
    Spindler, F
    Spencer, J
    Togni, A
    Rihs, G
    ORGANOMETALLICS, 1996, 15 (02) : 860 - 866
  • [39] Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: synthesis, characterization and catalytic transfer hydrogenation activity
    Byrne, Joseph P.
    Musembi, Pauline
    Albrecht, Martin
    DALTON TRANSACTIONS, 2019, 48 (31) : 11838 - 11847
  • [40] Synthesis, structure and characterization of picolyl and benzyl linked biphenyl nickel NHC complexes and their catalytic activity in Suzuki-Miyaura cross-coupling reactions
    Muniyappan, Nalluchamy
    Junaid, Qazi Mohammad
    Sabiah, Shahulhameed
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2021, 938