N-Heterocyclic Carbene C,S Palladium(II) π-Allyl Complexes: Synthesis, Characterization, and Catalytic Application In Allylic Amination Reactions

被引：30
|
作者：
Krishnan, Deepa [1 ]
Wu, Meiyi [1 ]
Chiang, Minyi [1 ]
Li, Yongxin [1 ]
Leung, Pak-Hing [1 ]
Pullarkat, Sumod A. [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
ORGANOMETALLICS | 2013年 / 32卷 / 08期
关键词：
TRANSITION-METAL-COMPLEXES; CROSS-COUPLING REACTIONS; ASYMMETRIC CATALYSIS; IRIDIUM COMPLEX; NHC LIGANDS; C-C; ENANTIOSELECTIVE ALLYLATION; STEREODIRECTING LIGANDS; SUBSTITUTION-REACTIONS; NICKEL(II) COMPLEXES;
D O I：
10.1021/om400110t
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A series of five-membered N-heterocyclic carbene C,S palladium(II) pi-allyl complexes were successfully developed and characterized. Structural analyses of these complexes revealed that the organopalladium chelates adopt a skew-envelope conformation with a trans disposition of the substituents on the metal chelate rings. Utilizing these C,S palladium(II) pi-allyl complexes as catalysts, a catalytic system for the allylic amination reaction has been developed. A series of C-N bond formations between amines and unsymmetrically substituted allylic carbonates could be catalyzed efficiently by complex (+/-)-9 in a regioselective manner.
引用
收藏
页码：2389 / 2397
页数：9
相关论文
共 50 条
  • [1] Palladium(II)-N-heterocyclic carbene complexes: synthesis, characterization and catalytic application
    Cekirdek, Suzan
    Yasar, Sedat
    Ozdemir, Ismail
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (06) : 423 - 431
  • [2] Palladium N-heterocyclic carbene complexes: Synthesis, characterization and catalytic properties in amination
    Ozdemir, Ismail
    Demir, Serpil
    Sahin, Onur
    Buyukgungor, Orhan
    Cetinkaya, Bekir
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (10-11) : 1555 - 1560
  • [3] Rigid hindered N-heterocyclic carbene palladium precatalysts: synthesis, characterization and catalytic amination
    Zhang, Fei-Yi
    Lan, Xiao-Bing
    Xu, Chang
    Yao, Hua-Gang
    Li, Tian
    Liu, Feng-Shou
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18) : 3292 - 3299
  • [4] N-Heterocyclic Carbene-Palladium(II) Complexes with Acridine Ligand: Synthesis, Characterization and Catalytic Applications
    Wang, Tao
    Xu, Kai
    Meng, Tuanjie
    Zhang, An'an
    Wang, Hongyu
    Shen, Sisi
    Liu, Lantao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (07) : 1794 - 1799
  • [5] Butylene linked palladium N-heterocyclic carbene complexes: Synthesis and catalytic properties
    Demir, Serpil
    Ozdemir, Ismail
    Arslan, Hakan
    VanDerveer, Don
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (13) : 2589 - 2593
  • [6] Synthesis, characterization and catalytic activity of novel N-heterocyclic carbene-palladium complexes
    Dogan, Oznur
    Gurbuz, Nevin
    Ozdemir, Ismail
    Cetinkaya, Bekir
    Sahin, Onur
    Buyukgungor, Orhan
    DALTON TRANSACTIONS, 2009, (35) : 7087 - 7093
  • [7] N-Heterocyclic carbene (NHC) palladium(II) complexes bearing chiral oxazoline ligands and their catalytic activities in allylic alkylation reactions
    Denizalti, Serpil
    Turkmen, Hayati
    Cetinkaya, Bekir
    TURKISH JOURNAL OF CHEMISTRY, 2014, 38 (05) : 679 - 685
  • [8] Synthesis and catalytic activity of ionic palladium N-heterocyclic carbene complexes
    Yasar, Sedat
    Akkoc, Mitat
    Ozdemir, Namik
    Ozdemir, Ismail
    TURKISH JOURNAL OF CHEMISTRY, 2019, 43 (06) : 1622 - +
  • [9] Bifunctional N-Heterocyclic Carbene Ferrocenyl Ligands - Synthesis and Palladium(II) Complexes
    Loxq, Pauline
    Daran, Jean-Claude
    Manoury, Eric
    Poli, Rinaldo
    Labande, Agnes
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2015, (04) : 609 - 616
  • [10] Synthesis, structural characterization and catalytic activity of two N-heterocyclic carbene-phosphine palladium(II) complexes
    Xu, Chen
    Hao, Xin-Qi
    Li, Zhen
    Dong, Xin-Ming
    Duan, Lu-Meng
    Wang, Zhi-Qiang
    Ji, Bao-Ming
    Song, Mao-Ping
    INORGANIC CHEMISTRY COMMUNICATIONS, 2012, 17 : 34 - 37
12345