Palladium complexes with cinnamyl and ionizable N-heterocyclic carbene ligands in the catalysis of the Suzuki—Miyaura reaction at room temperature

被引:0
作者
A. Yu. Chernenko [1 ]
M. E. Minyaev [2 ]
V. M. Chernyshev [1 ]
机构
[1] M. I. Platov South-Russian State Polytechnic University (NPI), 132 ul. Prosveschenya, Novocherkassk
[2] N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow
[3] Skolkovo Institute of Science and Technology, 30 Bolshoy bul., Skolkovo, Moscow
基金
俄罗斯科学基金会;
关键词
anionic complexes; catalysis; N-heterocyclic carbenes; palladium; Suzuki—Miyaura reaction;
D O I
10.1007/s11172-025-4563-0
中图分类号
学科分类号
摘要
The complexes [Pd(NHC)(cin)Cl] containing nitron-type N-heterocyclic carbene (NHC) ligands were synthesized. These ligands can acquire an anionic character due to the deprotonation of the NH-acidic arylamino group. The catalytic activity of the new complexes in the Suzuki—Miyaura reaction was evaluated. The η3-coordinated cinnamyl (cin) ligand, which is present in the complexes and acts as a reducing agent of Pd(ii) to Pd(0) in the presence of bases, promotes the rapid activation of the catalytic system. The complex with the 2,4-bis[2,6-diisopropylphenyl]-5-{[2,6-diisopropylphenyl]amino}-2,4-dihydro-3H-1,2,4-triazol-3-ylidene ligand showed a high efficiency in the catalysis of the cross-coupling of arylboronic acids with deactivated aryl chlorides and benzyl chlorides at 25 °C. © Springer Science+Business Media LLC 2025.
引用
收藏
页码:696 / 706
页数:10
相关论文
共 55 条
  • [1] Littke A.F., Fu G.C., Angew. Chem., Int. Ed, 41, (2002)
  • [2] Bedford R.B., Cazin C.S.J., Holder D., Coord. Chem. Rev, 248, (2004)
  • [3] Slagt V.F., de Vries A.H.M., de Vries J.G., Kellogg R.M., Org. Process Res. Dev, 14, (2010)
  • [4] Onoabedje E.A., Okoro U.C., Synth. Commun, 49, (2019)
  • [5] Kurokhtina A.A., Larina E.V., Lagoda N.A., Schmidt A.F., Russ. Chem. Bull, 73, (2024)
  • [6] Fortman G.C., Nolan S.P., Chem. Soc. Rev, 40, (2011)
  • [7] Valente C., Calimsiz S., Hoi K.H., Mallik D., Sayah M., Organ M.G., Angew. Chem., Int. Ed, 51, (2012)
  • [8] Diner C., Organ M.G., Organometallics, 38, (2019)
  • [9] Shevchenko M.A., Pasyukov D.V., Minyaev M.E., Chernyshev V.M., Russ. Chem. Bull, 73, (2024)
  • [10] Bellotti P., Koy M., Hopkinson M.N., Glorius F., Nat. Rev. Chem, 5, (2021)