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
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
  • [41] Mixed Phosphite/N-Heterocyclic Carbene Complexes: Synthesis, Characterization and Catalytic Studies
    Diebolt, Olivier
    Jurcik, Vaclav
    da Costa, Rosenildo Correa
    Braunstein, Pierre
    Cavallo, Luigi
    Nolan, Steven P.
    Slawin, Alexandra M. Z.
    Cazin, Catherine S. J.
    ORGANOMETALLICS, 2010, 29 (06) : 1443 - 1450
  • [42] Synthesis, characterization and catalytic properties of cationic N-heterocyclic carbene silver complexes
    Atli, Deniz Demir
    TURKISH JOURNAL OF CHEMISTRY, 2021, 45 (03) : 577 - +
  • [43] Synthesis, characterization, and catalytic screening reactions of N-heterocyclic carbene-containing iron carbonyl complexes
    Mann, Jeff
    Chmely, Stephen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [44] Synthesis, structure and catalytic application of palladium(II) complexes bearing N-heterocyclic carbenes and phosphines
    Herrmann, WA
    Böhm, VPW
    Gstöttmayr, CWK
    Grosche, M
    Reisinger, CP
    Weskamp, T
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 616 - 628
  • [45] Synthesis, characterization and catalytic properties of an N-heterocyclic carbene palladium-based complex
    Ozdemir, Ismail
    Arslan, Hakan
    Demir, Serpil
    VanDerveer, Don
    Cetinkaya, Bekir
    INORGANIC CHEMISTRY COMMUNICATIONS, 2008, 11 (12) : 1462 - 1465
  • [46] New chelating N-heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties
    Yang, Liangru
    Liu, Yaowen
    Diao, Xiaoqiong
    Zeng, Xianggui
    Xiao, Yongmei
    Yuan, Jinwei
    Mao, Pu
    APPLIED ORGANOMETALLIC CHEMISTRY, 2024, 38 (09)
  • [47] Indazolin-s-ylidene N-Heterocyclic Carbene Complexes of Rhodium, Palladium, and Gold: Synthesis, Characterization, and Catalytic Hydration of Alkynes
    Zhou, Yang
    Liu, Qingjie
    Lv, Weifeng
    Pang, Qingyu
    Ben, Rong
    Qian, Yong
    Zhao, Jing
    ORGANOMETALLICS, 2013, 32 (13) : 3753 - 3759
  • [48] Fluoroalkylated N-heterocyclic carbene complexes of palladium
    Xu, LJ
    Chen, WP
    Bickley, JF
    Steiner, A
    Xiao, JL
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 598 (02) : 409 - 416
  • [49] Microwave-Assisted Synthesis of N-Heterocyclic Carbene-Palladium(II) Complexes
    Winkelmann, Ole H.
    Navarro, Oscar
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (01) : 212 - 214
  • [50] Synthesis and characterization of (N-heterocyclic carbene)Pd(allyl)chlorides and their performance in catalytic cross-coupling reactions.
    Navarro-Fernandez, O
    Viciu, MS
    Stevens, ED
    Nolan, SP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U131 - U131