Palladium(II) complexes featuring bidentate pyridine–triazole ligands: Synthesis, structures, and catalytic activities for Suzuki–Miyaura coupling reactions

Jindabot, Sudarat; Teerachanan, Kriengkamol; Thongkam, Pech; Kiatisevi, Supavadee; Khamnaen, Tossapol; Phiriyawirut, Phairat; Charoenchaidet, Sumate; Sooksimuang, Thanasat; Kongsaeree, Palangpon; Sangtrirutnugul, Preeyanuch

doi:10.1016/j.jorganchem.2013.10.046

Cited by 40 publications

(31 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Pd II ions were coordinated by two chloride ions and two triazole N donors of the ligands, forming a six membered ring with a boat conformation. The Pd–N trz bond distances [2.013–2.032 Å] and the N trz –Pd–N trz bite angles [85.67(7) o and 87.10(7) o ] are within the expected ranges and comparable to previously reported structures of Pd‐triazolyl complexes ,–,. Interestingly, the crystal structures reveal no Pd⋅⋅⋅O interactions but there is a hydrogen bonding between the OH group on sp 3 C atom and the O atom of DMF with a contact distance of 1.901 Å and 1.930 Å, for 6 and 8 , respectively (Figure and ).…”

Section: Resultssupporting

confidence: 87%

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

et al. 2018

Self Cite

View full text Add to dashboard Cite

PdII‐bis(triazolyl)phenylmethanol complexes bearing different groups (i. e., H, OMe, OH, COOH) directly attached to the benzyl rings were explored as precatalysts for copper‐free Sonogashira and Suzuki–Miyaura coupling reactions in water. Crystal structures reveal a bidentate N,N binding mode of the bis(triazolyl) ligands affording a distorted square planar PdII complexes. With the exception of the phenol‐substituted bis(triazolyl) ligands, the other three Pd complexes exhibited high activities toward Suzuki–Miyaura coupling reactions. Transmission electron microscopy (TEM) study and PPh3 poisoning experiments confirm that bis(triazoly)‐stabilized Pd nanoparticles (Pd NPs) were generated in situ during the catalytic reactions and involved as one of the active catalytic species in the Suzuki–Miyaura cross coupling.

show abstract

Section: Resultssupporting

confidence: 87%

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…24 Reactions of Cu(OTf) 2 (2), NN' py (3)] in good yields (81-83% yields). For comparison, the analogous Cu(bpy) 2 (OTf) 2 was also prepared under similar reaction conditions, giving blue crystalline solids as the product 4 in 87% yield.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…2-azidopyridine and 2-(4-R-1,2,3-triazol-1yl)pyridine [R = C 6 H 5 (NN' Ph ), n-C 6 H 13 (NN' hex ), NC 5 H 4 (NN' py )] were prepared according to the literature. 24 1 H (500.1 MHz) NMR spectra were acquired on Bruker AV-500 spectrometer equipped with a 5 mm proton/BBI probe at room temperature and referenced to protic impurities in the deuterated solvent. Elemental analyses were conducted at Chemistry department, Mahidol University.…”

Section: General Proceduresmentioning

confidence: 99%

Pyridine–triazole ligands for copper-catalyzed aerobic alcohol oxidation

et al. 2015

Self Cite

View full text Add to dashboard Cite

A series of [Cu(NN')]2(OTf)2 complexes containing pyridine-triazole ligands [OTf = OSO2CF3; NN' = NN'Ph (1), NN'hex (2), NN'py (3)] with different substituents at the triazole N4 position or 2,2'-bipyridine (bpy; 4) have been synthesized. Crystal structures of 1 and 3 reveal a trans-isomer with strong preference for regular-type triazole coordination (for 3) whereas the Cu-bipyridine complex 4 is more stable in a cis-form. Cyclic voltammetry of 1-4 suggest that the electron-donating strength follows the trend: bpy > NN'py > NN'hex ~ NN'Ph. The catalyst systems consisting of 5 mol% CuOTf2/NN'/TEMPO (TEMPO = (2,2,6,6-tetramethylpiperidin-1-yl)oxy) in the presence of 2x2.0 cm 2 Cu 0 sheets as a reducing agent and 10 mol% N-methylimidazole (NMI) exhibit good activities for aerobic oxidation of benzyl alcohol to benzaldehyde. Catalytic studies have shown that the activities were higher with more electron-rich N-based ligands. Furthermore, oxidation of aliphatic alcohols such as 1-hexanol and 2-methyl-1-pentanol using the Cu catalyst system with the NN'py ligand at room temperature afforded the corresponding aldehydes in >99% and 46% yields, respectively after 24 h.

show abstract

“…[1][2][3][4][5][6][7][8][9] As far as we know, many different types of phosphine ligand have been discovered for Suzuki-Miyaura cross-coupling reaction. [12,13] Therefore, in the past few years, great advances have been made in developing active and efficient catalysts by phosphine-free ligands. [12,13] Therefore, in the past few years, great advances have been made in developing active and efficient catalysts by phosphine-free ligands.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Bulky α‐Diimine Palladium Complexes for Suzuki‐Miyaura Cross‐Coupling Reaction

Huo

Liu

et al. 2017

Chin. J. Chem.

View full text Add to dashboard Cite

A series of bulky 9,10-dihydro-9,10-ethanoanthracene-11,12-diimine methyl palladium chloride complexes (C1 -C6) with different steric and electronic substituent have been applied in Suzuki-Miyaura cross-coupling reactions. The influence of these substituents was investigated by comparing the catalytic performance of the complexes in the cross-coupling reactions and it can be found that the complex with bulky and electron-donating substituent is facilitated for the cross-coupling reaction of aryl halides with arylboronic acids under ambient atmosphere. The most active complex shows a wide substrate scope in excellent yields using very low catalyst concentration of 0.01 mol%.

show abstract

Palladium(II) complexes featuring bidentate pyridine–triazole ligands: Synthesis, structures, and catalytic activities for Suzuki–Miyaura coupling reactions

Cited by 40 publications

References 47 publications

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

Pyridine–triazole ligands for copper-catalyzed aerobic alcohol oxidation

Highly Efficient Bulky α‐Diimine Palladium Complexes for Suzuki‐Miyaura Cross‐Coupling Reaction

Contact Info

Product

Resources

About