Catalytic umpolung allylation of aldehydes by π-allylpalladium complexes containing bidentate N-heterocyclic carbene ligands

被引:64
|
作者
Barczak, Nicholas T. [1 ]
Grote, Robin E. [1 ]
Jarvo, Elizabeth R. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
PALLADIUM COMPLEXES; ELECTROPHILIC SUBSTITUTION; MECHANISM; REACTIVITY; ALCOHOLS;
D O I
10.1021/om700605y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of pi-allylpalladium complexes with neutral monodentate and bidentate ligands were prepared and examined for their ability to undergo stoichiometric umpolung allylation reactions with benzaldehyde. Neutral bidentate N-heterocyclic carbene ligands promote nucleophilic attack. Catalytic allylation reactions of aromatic and aliphatic aldehydes are reported.
引用
收藏
页码:4863 / 4865
页数:3
相关论文
共 50 条
  • [31] 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
  • [32] N-heterocyclic carbene tethered amido complexes of palladium and platinum
    Cross, Warren B.
    Daly, Christopher G.
    Ackerman, Rachel L.
    George, Ian R.
    Singh, Kuldip
    DALTON TRANSACTIONS, 2011, 40 (02) : 495 - 505
  • [33] N-Heterocyclic carbene (NHC) organocatalysis using aliphatic aldehydes
    Barik, Shilpa
    Biju, Akkattu T.
    CHEMICAL COMMUNICATIONS, 2020, 56 (99) : 15484 - 15495
  • [34] Allylcopper Intermediates with N-Heterocyclic Carbene Ligands: Synthesis, Structure, and Catalysis
    Russo, Vincenzo
    Herron, Jessica R.
    Ball, Zachary T.
    ORGANIC LETTERS, 2010, 12 (02) : 220 - 223
  • [35] N-Heterocyclic Carbene-Catalyzed Umpolung of Imines for the Enantioselective Synthesis of Dihydroquinoxalines
    Das, Tamal Kanti
    Ghosh, Avik
    Balanna, Kuruva
    Behera, Pradipta
    Gonnade, Rajesh G.
    Marelli, Udaya Kiran
    Das, Abhijit Kumar
    Biju, Akkattu T.
    ACS CATALYSIS, 2019, 9 (05) : 4065 - 4071
  • [36] Iridium Complexes of CCC-Pincer N-Heterocyclic Carbene Ligands: Synthesis and Catalytic C-H Functionalization
    Chianese, Anthony R.
    Mo, Allen
    Lampland, Nicole L.
    Swartz, Raymond L.
    Bremer, Paul T.
    ORGANOMETALLICS, 2010, 29 (13) : 3019 - 3026
  • [37] Photofunctional Platinum Complexes Featuring N-heterocyclic Carbene-Based Pincer Ligands
    Lin, Wan-Jung
    Naziruddin, Abbas Raja
    Chen, Yu-Hsuan
    Sun, Bian-Jian
    Chang, A. Hsiu Hwa
    Wang, Wen-Jwu
    Hwang, Wen-Shu
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (03) : 728 - 739
  • [38] Manganese(iii) complexes stabilized with N-heterocyclic carbene ligands for alcohol oxidation catalysis
    Rigoni, Giacomo
    Nylund, Pamela V. S.
    Albrecht, Martin
    DALTON TRANSACTIONS, 2023, 52 (23) : 7992 - 8002
  • [39] Catalytic deuteration of silanes mediated by N-heterocyclic carbene-Ir(III) complexes
    Fortman, George C.
    Jacobsen, Heiko
    Cavallo, Luigi
    Nolan, Steven P.
    CHEMICAL COMMUNICATIONS, 2011, 47 (34) : 9723 - 9725
  • [40] Iridium phosphine abnormal N-heterocyclic carbene complexes in catalytic hydrogen transfer reactions
    Gong, Xue
    Zhang, Hong
    Li, Xingwei
    TETRAHEDRON LETTERS, 2011, 52 (43) : 5596 - 5600