Palladium(II) pyrazolyl-pyridyl complexes containing a sterically hindered N-heterocyclic carbene moiety for the Suzuki-Miyaura cross-coupling reaction

被引:25
作者
Luconi, Lapo [1 ]
Gafurov, Zufar [2 ]
Rossin, Andrea [1 ]
Tuci, Giulia [1 ]
Sinyashin, Oleg [2 ]
Yakhvarov, Dmitry [2 ,3 ]
Giambastiani, Giuliano [1 ,3 ]
机构
[1] CNR, ICCOM, Inst Chem OrganoMetall Cpds, Via Madonna del Piano 10, I-50019 Florence, Italy
[2] Russian Acad Sci, AE Arbuzov Inst Organ & Phys Chem, Arbuzov Str 8, Kazan 420088, Russia
[3] Kazan Fed Univ, Kazan 420008, Russia
关键词
NHC-containing ligand; Palladium complexes; Suzuki-Miyaura coupling; ORTHO-SUBSTITUTED BIARYLS; OXIDATIVE ADDITION; CATALYTIC-ACTIVITY; LIGANDS; POLYMERIZATION;
D O I
10.1016/j.ica.2017.03.026
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cationic palladium complexes stabilized by a tridentate neutral {N, N, C} ligand containing a sterically hindered N-heterocyclic carbene (NHC) moiety have been prepared and characterized. The nature of the anionic counterion in the palladium complex has been varied to get crystals suitable for X-ray diffraction. The square planar structure of one of these complexes along with the axial contribution of the sterically hindered NHC fragment has been confirmed by X-ray analysis. In addition, all the isolated [{kappa(3)-N, N, C} (PdCl)-Cl-II]X-+(-) [X- = Cl, PF6, BF4, B(C6H3Cl2)(4)] ion pairs have been scrutinized as catalysts in the cross-coupling Suzuki-Miyaura reaction between phenylboronic acid and variably substituted halo-aryl acceptors. Selected issues from this series have shown improved catalyst turn-over frequencies (TOFs) with respect to structurally related catalytic systems of the state-of-the-art. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:100 / 105
页数:6
相关论文
共 36 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]   BIS(BENZONITRILE)DICHLORO COMPLEXES OF PALLADIUM AND PLATINUM [J].
ANDERSON, GK ;
LIN, M .
INORGANIC SYNTHESES, 1990, 28 :60-63
[3]   Synthesis of some halogenated tetraarylborates [J].
Anulewicz-Ostrowska, R ;
Klis, T ;
Krajewski, D ;
Lewandowski, B ;
Serwatowski, J .
TETRAHEDRON LETTERS, 2003, 44 (39) :7329-7331
[4]   Pyrazole-Based PCN Pincer Complexes of Palladium(II): Mono- and Dinuclear Hydroxide Complexes and Ligand Rollover C-H Activation [J].
Bailey, Wilson D. ;
Luconi, Lapo ;
Rossin, Andrea ;
Yakhvarov, Dmitry ;
Flowers, Sarah E. ;
Kaminsky, Werner ;
Kemp, Richard A. ;
Giambastiani, Giuliano ;
Goldberg, Karen I. .
ORGANOMETALLICS, 2015, 34 (16) :3998-4010
[5]   Distinct mechanisms for the oxidative addition of chloro-, bromo-, and lodoarenes to a bisphosphine palladium(0) complex with hindered ligands [J].
Barrios-Landeros, F ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6944-6945
[6]   Effect of Ligand Steric Properties and Halide Identity on the Mechanism for Oxidative Addition of Haloarenes to Trialkylphosphine Pd(0) Complexes [J].
Barrios-Landeros, Fabiola ;
Carrow, Brad P. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) :8141-8154
[7]   PEPPSI-Type Palladium Complexes Containing Basic 1,2,3-Triazolylidene Ligands and Their Role in Suzuki-Miyaura Catalysis [J].
Canseco-Gonzalez, Daniel ;
Gniewek, Andrzej ;
Szulmanowicz, Michal ;
Mueller-Bunz, Helge ;
Trzeciak, Anna M. ;
Albrecht, Martin .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) :6055-6062
[8]   [B(3,5-C6H3Cl2)4]- as a Useful Anion for Organometallic Chemistry [J].
Chaplin, Adrian B. ;
Weller, Andrew S. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (32) :5124-5128
[9]   [Pd(IPr*)(cinnamyl)Cl]: An Efficient Pre-catalyst for the Preparation of Tetra-ortho-substituted Biaryls by Suzuki-Miyaura Cross-Coupling [J].
Chartoire, Anthony ;
Lesieur, Mathieu ;
Falivene, Laura ;
Slawin, Alexandra M. Z. ;
Cavallo, Luigi ;
Cazin, Catherine S. J. ;
Nolan, Steven P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (15) :4517-4521
[10]   NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis [J].
Crabtree, RH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5451-5457