Impact of the N-Heterocyclic Carbene (NHC) Ligand on the trans-[Pd(NHC)(NH2 n Bu)Cl2] Precatalyst Architecture in C-N Bond-Forming Reactions

被引：0
作者：
Pozsoni, Nestor Bracho [1 ,2 ]
Nahra, Fady [1 ,2 ,3 ]
van Hecke, Kristof [1 ,2 ]
Cazin, Catherine S. J. [1 ,2 ]
Nolan, Steven P. [1 ,2 ]
机构：
[1] Univ Ghent, Dept Chem, B-9000 Ghent, Belgium
[2] Univ Ghent, Ctr Sustainable Chem, B-9000 Ghent, Belgium
[3] VITO Flemish Inst Technol Res, Mat & Chem MATCH Unit, B-2400 Mol, Belgium
来源：
ORGANOMETALLICS | 2024年 / 43卷 / 22期
关键词：
CROSS-COUPLING REACTIONS; PALLADIUM CATALYSTS; CONVERSION;
D O I：
10.1021/acs.organomet.4c00419
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Two straightforward synthetic procedures leading to air- and moisture-stable trans-[Pd(NHC)(NH2 n Bu)Cl2] precatalysts are presented. These complexes, obtained by adding n-butylamine to [Pd(NHC)(mu-Cl)Cl]2 or trans-[Pd(NHC)(DMS)Cl2] precursors (DMS, dimethyl sulfide), demonstrate superior catalytic activity compared to their DMS counterparts in Buchwald-Hartwig amination reactions. Utilizing a more sustainable solvent (2-MeTHF), the catalyst loading was halved to 0.1 mol %, establishing this new system as a highly efficient and environmentally more friendly alternative to previous systems.
引用
收藏
页码：2963 / 2971
页数：9
相关论文
共 39 条
  • [31] 2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry
    Pace, Vittorio
    Hoyos, Pilar
    Castoldi, Laura
    Dominguez de Maria, Pablo
    Alcantara, Andres R.
    [J]. CHEMSUSCHEM, 2012, 5 (08) : 1369 - 1379
  • [32] Amines as Activating Ligands for Phosphine Palladium(II) Precatalysts: Effect of Amine Ligand Identity on the Catalyst Efficiency
    Pierce, Jordan K.
    Hiatt, Lindsey D.
    Howard, James R.
    Hu, Huaiyuan
    Qu, Fengrui
    Shaughnessy, Kevin H.
    [J]. ORGANOMETALLICS, 2022, 41 (24) : 3861 - 3871
  • [33] Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos)
    Rodstein, Ilja
    Prendes, Daniel Sowa
    Wickert, Leon
    Paassen, Maurice
    Gessner, Viktoria H.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (22) : 14674 - 14683
  • [34] Roose P., 2015, Ullmann's Encyclopedia of Industrial Chemistry, P1
  • [35] Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions
    Ruiz-Castillo, Paula
    Buchwald, Stephen L.
    [J]. CHEMICAL REVIEWS, 2016, 116 (19) : 12564 - 12649
  • [36] Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species
    Shaughnessy, Kevin H.
    [J]. ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (3-4) : 180 - 194
  • [37] Recent advances in sustainable N-heterocyclic carbene-Pd(II)-pyridine (PEPPSI) catalysts: A review
    Vasu, Govardhana Reddy Peddiahgari
    Venkata, Krishna Reddy Motakatla
    Kakarla, Raghava Reddy
    Ranganath, Kalluri V. S.
    Aminabhavi, Tejraj M.
    [J]. ENVIRONMENTAL RESEARCH, 2023, 225
  • [38] Buchwald-Hartwig amination of aryl esters and chlorides catalyzed by the dianisole-decorated Pd-NHC complex
    Zheng, Di-Zhong
    Xiong, Hong-Gang
    Song, A-Xiang
    Yao, Hua-Gang
    Xu, Chang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (10) : 2096 - 2101
  • [39] A simple synthetic entryway into palladium cross-coupling catalysis
    Zinser, Caroline M.
    Nahra, Fady
    Brill, Marcel
    Meadows, Rebecca E.
    Cordes, David B.
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    Cazin, Catherine S. J.
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (57) : 7990 - 7993
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