Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts

被引:4
|
作者
Zhong, Chuntao [1 ]
Tang, Huiling [1 ]
Cui, Benqiang [1 ]
Shi, Yanhui [1 ]
Cao, Changsheng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Suzuki reaction; Quaternary ammonium salts; Palladium NHC; Diarylmethanes; C-N BOND; BENZYLTRIMETHYLAMMONIUM SALTS; ARYL; DIARYLMETHANES; ACIDS; ACTIVATION; HYDROGENATION; ALKYLARENES; COMPLEXES; ARYLATION;
D O I
10.1007/s11164-022-04795-6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed Suzuki cross-coupling of benzyl ammonium triflates via activation of a Csp(3)-N bond to construct a Csp(3)-Csp(2) bond is described. Various boronic acids can be coupled with a range of benzylamine-derived quaternary ammonium salts in 1:1 molar ratio by the bench-stable N-heterocyclic carbene palladium complex, SIPr-PdCl2-Py to afford diarylmethane derivatives. This reaction exhibits a wide substrate scope and functional group tolerance. Direct arylation of benzylamine in a one-pot process and the gram-scale reaction can be performed successfully.
引用
收藏
页码:4017 / 4032
页数:16
相关论文
共 50 条
  • [21] Carbon-Sulfur Coupling Reactions Catalyzed by Pd-NHC Complex
    Shi, Yanhui
    Cai, Zhengyuan
    Guan, Pei
    Pang, Guangsheng
    SYNLETT, 2011, (14) : 2090 - 2096
  • [22] Recyclable supported Pd-NHC catalytic systems for the copper-free Sonogashira cross-coupling in flow
    Penafiel, I.
    Martinez-Lombardia, A.
    Godard, C.
    Claver, C.
    Lapkin, A.
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2018, 9 : 69 - 75
  • [23] Selective and general exhaustive cross-coupling of di-chloroarenes with a deficit of nucleophiles mediated by a Pd-NHC complex
    Groombridge, Benjamin J.
    Goldup, Stephen M.
    Larrosa, Igor
    CHEMICAL COMMUNICATIONS, 2015, 51 (18) : 3832 - 3834
  • [24] Nanoparticles Pd-Catalyzed Highly Efficient Suzuki Cross-Coupling Reaction
    Zhao, Xiaoxia
    Chang, Honghong
    Li, Xing
    Wei, Wenlong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (08) : 1650 - 1656
  • [25] Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters
    Buchspies, Jonathan
    Pyle, Daniel J.
    He, Huixin
    Szostak, Michal
    MOLECULES, 2018, 23 (12):
  • [26] Pd-catalyzed synthesis of β-biarylacryl ferrocenes via Suzuki cross-coupling
    Song, QB
    Lin, RX
    Yang, ZP
    Qi, CZ
    MOLECULES, 2005, 10 (06) : 634 - 639
  • [27] Pd-catalyzed Suzuki cross-coupling reactions of glycerol arylboronic esters
    Nichele, Tatiana Z.
    Favero, Cristiano
    Monteiro, Adriano L.
    CATALYSIS COMMUNICATIONS, 2009, 10 (05) : 693 - 696
  • [28] Selective Cross-Coupling of (Hetero)aryl Halides with Ammonia To Produce Primary Arylamines using Pd-NHC Complexes
    Lombardi, Christopher
    Day, Jonathan
    Chandrasoma, Nalin
    Mitchell, David
    Rodriguez, Michael J.
    Farmer, Jennifer L.
    Organ, Michael G.
    ORGANOMETALLICS, 2017, 36 (02) : 251 - 254
  • [29] Nickel-catalyzed Suzuki cross-coupling reaction of alkyl triaryl phosphonium salts
    Zhu, Meiqi
    Yu, Wen
    Zhong, Qin
    Cui, Benqiang
    Cao, Changsheng
    Shi, Yanhui
    TETRAHEDRON, 2023, 135
  • [30] Mechanism of the Suzuki-Miyaura Cross-Coupling Reaction Mediated by [Pd(NHC)(allyl)Cl] Precatalysts
    Magi Meconi, Giulia
    Vummaleti, Sai Vikrama Chaitanya
    Antonio Luque-Urrutia, Jesus
    Belanzoni, Paola
    Nolan, Steven P.
    Jacobsen, Heiko
    Cavallo, Luigi
    Sola, Miguel
    Poater, Albert
    ORGANOMETALLICS, 2017, 36 (11) : 2088 - 2095