Palladium-Catalyzed Suzuki-Miyaura cross-coupling reactions employing hydrazone-thioether ligands in aqueous media under IR-irradiation

被引:0
作者
Reyes-Deloso, Alberto [1 ]
Penieres-Carrillo, Jose Guillermo [1 ]
Rios-Guerra, Hulme [1 ]
Lagunas-Rivera, Selene [2 ]
Galvan-Garcia, Emir A. [3 ]
Gomez-Balderas, Rodolfo [3 ]
Ortega-Jimenez, Fernando [1 ]
机构
[1] UNAM, Fac Estudios Super Cuautitlan, Dept Ciencias Quim, Ave 1ro Mayo S-N, Cuautitlan 54740, Estado De Mexic, Mexico
[2] Univ Guanajuato, Dept Quim, Catedra CONACyT, Noria Alta S-N, Guanajuato 36050, Guanajuato, Mexico
[3] Univ Nacl Autonoma Mexico, Fac Estudios Super Cuautitlan, Unidad Invest Multidisciplinaria, Lab Fisicoquim Analit, Cuautitlan 54714, Estado De Mexic, Mexico
关键词
Hydrazone-thioether ligands; Palladium-catalyzed; Cross-coupling reaction; Aqueous media; IR-irradition; SULFENYLATED CARBONYL-COMPOUNDS; SULFUR-CONTAINING PALLADACYCLES; C-C; MIZOROKI-HECK; SOLVENT-FREE; PROPARGYLIC ALCOHOLS; ARYL CHLORIDES; PD(II) COMPLEX; EFFICIENT; WATER;
D O I
10.1016/j.molstruc.2023.136562
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
An in situ catalytic system was generated based on hydrazone-thioether ligands and Pd(OAc)2. It provided excellent catalytic activity in the Suzuki-Miyaura cross-coupling reactions between aryl halides and arylboronic acids in aqueous medium and under IR irradiation. The resulting coupled products were obtained in short re-action times, with low catalyst loads and in good to excellent yields. Density functional theory based compu-tations were applied to characterize the probable structure of the dimeric complex formed between the hydrazone and Pd(OAc)2, afterwards structure was confirmed by experimental analysis of IR and ESI mass spectrometry.
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页数:9
相关论文
共 69 条
  • [51] Ultrasound effect on Suzuki reactions.: 1.: Synthesis of unsymmetrical biaryls
    Polácková, V
    Hut'ka, M
    Toma, T
    [J]. ULTRASONICS SONOCHEMISTRY, 2005, 12 (1-2) : 99 - 102
  • [52] Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water
    Ramakrishna, V.
    Reddy, N. Dastagiri
    [J]. DALTON TRANSACTIONS, 2017, 46 (26) : 8598 - 8610
  • [53] Microwave assisted Suzuki-Miyaura and Mizoroki-Heck cross-couplings catalyzed by non-symmetric Pd(II) CNS pincers supported by iminophosphorane ligands
    Ramirez-Rave, Sandra
    Morales-Morales, David
    Grevy, Jean-Michel
    [J]. INORGANICA CHIMICA ACTA, 2017, 462 : 249 - 255
  • [54] Fluorinated N-Heterocyclic carbene complexes. Applications in catalysis
    Rufino-Felipe, Ernesto
    Valdes, Hugo
    Manuel German-Acacio, Juan
    Reyes-Marquez, Viviana
    Morales-Morales, David
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 921
  • [55] Mixed phosphine/N-heterocyclic carbene palladium complexes: synthesis, characterization and catalytic use in aqueous Suzuki-Miyaura reactions
    Schmid, Thibault E.
    Jones, Dale C.
    Songis, Olivier
    Diebolt, Olivier
    Furst, Marc R. L.
    Slawin, Alexandra M. Z.
    Cazin, Catherine S. J.
    [J]. DALTON TRANSACTIONS, 2013, 42 (20) : 7345 - 7353
  • [56] Synthesis and evaluation of 5-phenyl-1H-1,4-benzodiazepin-2(3H)-one-based palladium complexes as precatalysts in C-C bond forming reactions
    Spencer, J
    Sharratt, DP
    Dupont, J
    Monteiro, AL
    Reis, VI
    Stracke, MP
    Rominger, F
    McDonald, IM
    [J]. ORGANOMETALLICS, 2005, 24 (23) : 5665 - 5672
  • [57] Stensitzki T, 2018, NAT CHEM, V10, P126, DOI [10.1038/NCHEM.2909, 10.1038/nchem.2909]
  • [58] Palladium fabricated on boehmite as an organic-inorganic hybrid nanocatalyst for C-C cross coupling and homoselective cycloaddition reactions
    Tahmasbi, Bahman
    Ghorbani-Choghamarani, Arash
    Moradi, Parisa
    [J]. NEW JOURNAL OF CHEMISTRY, 2020, 44 (09) : 3717 - 3727
  • [59] Magnetic MCM-41 nanoparticles as a support for the immobilization of a palladium organometallic catalyst and its application in C-C coupling reactions
    Tahmasbi, Bahman
    Ghorbani-Choghamarani, Arash
    [J]. NEW JOURNAL OF CHEMISTRY, 2019, 43 (36) : 14485 - 14501
  • [60] Pd(0)-Arg-boehmite: As Reusable and Efficient Nanocatalyst in Suzuki and Heck Reactions
    Tahmasbi, Bahman
    Ghorbani-Choghamarani, Arash
    [J]. CATALYSIS LETTERS, 2017, 147 (03) : 649 - 662