Telomerization of butadiene with ethanol mediated by palladium N-heterocyclic carbene catalysts

被引:3
|
作者
Palio, Lorenzo [1 ,2 ]
Dumont, Clement [1 ]
Suisse, Isabelle [1 ]
Sauthier, Mathieu [1 ]
Nolan, Steven P. [2 ]
机构
[1] Univ Lille, Univ Artois, UMR 8181 UCCS Un Catalyse & Chim Solide, CNRS,ENSC, F-59000 Lille, France
[2] Univ Ghent, Ctr Sustainable Chem, Dept Chem, Krijgslaan 281 S-3, B-9000 Ghent, Belgium
关键词
CROSS-COUPLING REACTIONS; EFFICIENT CATALYST; SYNTHETIC ROUTES; COMPLEXES; 1,3-BUTADIENE; NHC; 1,3-DIENES; REACTIVITY; ALCOHOLS;
D O I
10.1016/j.jcat.2023.115216
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
The telomerization reaction of dienes with alcohols mediated by organopalladium complexes represents a versatile method to convert butadiene into value-added chemicals. In this contribution, we have examined the catalytic behavior of a series of well-defined palladium N-heterocyclic carbene precatalysts (Pd-NHC) in the telomerization of butadiene with ethanol. The bulky and less sterically demanding NHC ligands greatly influence yields and selectivity towards the linear product. With more hindered NHC ligands, the branched product is obtained in unprecedented higher amounts. The telomerization of butadiene with the renewable solketal leads to selective and complete conversion to product in minutes.
引用
收藏
页数:8
相关论文
共 50 条
  • [21] 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
  • [22] N-Heterocyclic Carbene-Phosphinidenide Complexes as Hydroboration Catalysts
    Bhattacharjee, Jayeeta
    Bockfeld, Dirk
    Tamm, Matthias
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (02) : 1098 - 1109
  • [23] Cobalt(-I)- and Rhodium(-I)-Mediated Dearylation of N-Aryl N-Heterocyclic Carbene Ligands
    Wang, Peng
    Cheng, Jun
    Wang, Dongyang
    Yang, Chengbo
    Leng, Xuebing
    Deng, Liang
    ORGANOMETALLICS, 2020, 39 (15) : 2871 - 2877
  • [24] Arylation of heterocyclic compounds by benzimidazole-based N-heterocyclic carbene-palladium(II) complexes
    Sahin, Neslihan
    Gurbuz, Nevin
    Karabiyik, Hande
    Karabiyik, Hasan
    Ozdemir, Ismail
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 907 (907)
  • [25] Simple Silver Salts and Palladium Bis(N-heterocyclic carbene) Complexes As Complementary Catalysts for the Nazarov Cyclization
    Subramanium, Sri S.
    Handa, Sachin
    Miranda, Anthea J.
    Slaughter, LeGrande M.
    ACS CATALYSIS, 2011, 1 (10): : 1371 - 1374
  • [26] Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis
    Meiries, Sebastien
    Le Duc, Gaetan
    Chartoire, Anthony
    Collado, Alba
    Speck, Klaus
    Arachchige, Kasun S. Athukorala
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (51) : 17358 - 17368
  • [27] N-Heterocyclic Carbene-Derived Carbon Disulfide Radical Ligands for Palladium Diradicals
    Park, Subin
    Hwang, Jeong-Yoon
    Shin, Jeongcheol
    Kim, Youngsuk
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (41) : 28508 - 28515
  • [28] Direct Synthesis of N-Heterocyclic Carbene-Stabilized Copper Nanoparticles from an N-Heterocyclic Carbene-Borane
    Frogneux, Xavier
    Hippolyte, Laura
    Mercier, Dimitri
    Portehault, David
    Chaneac, Corinne
    Sanchez, Clement
    Marcus, Philippe
    Ribot, Francois
    Fensterbank, Louis
    Carenco, Sophie
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (49) : 11481 - 11485
  • [29] Bidentate Chelating N-Heterocyclic Carbene Complexes of Palladium: Synthesis and Structure
    Nan, Guangming
    Qin, Yuancheng
    Wei, Zhijun
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2012, 42 (02) : 285 - 290
  • [30] 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 - +