Suzuki–Miyaura cross-coupling reaction of aryl bromides catalyzed by palladium(II) pyridoxal hydrazone complexes

Pandiarajan, Devaraj; Ramesh, Rengan

doi:10.1016/j.jorganchem.2012.02.010

Cited by 36 publications

(12 citation statements)

References 56 publications

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“…Unfortunately, inorganic bases, which are soluble in water, demonstrated low activity in the present protocol (Table 1, entries 1 – 7 ). It is a well-known fact that many reports have described use of alcohol as co-solvent in the Suzuki-Miyaura reaction [43,44,45,46,47,48]. Therefore we studied the use of alcohol as co-solvent in this protocol.…”

Section: Resultsmentioning

confidence: 99%

A Simple Hydrophilic Palladium(II) Complex as a Highly Efficient Catalyst for Room Temperature Aerobic Suzuki Coupling Reactions in Aqueous Media

et al. 2014

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Abstract:A study on room temperature Suzuki cross-coupling in an aqueous medium was carried out using a simple hydrophilic palladium (II) complex, trans-PdCl 2 (NH 2 CH 2 COOH) 2 as catalyst in the presence of K 2 CO 3 in air. This approach with a comparatively inexpensive and hydrophilic catalyst, mild reaction condition and aqueous media exhibits excellent catalytic activity towards the Suzuki coupling of aryl bromides and arylboronic acids, and good yields were obtained in the Suzuki coupling of activated aryl chlorides.

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Section: Resultsmentioning

confidence: 99%

A Simple Hydrophilic Palladium(II) Complex as a Highly Efficient Catalyst for Room Temperature Aerobic Suzuki Coupling Reactions in Aqueous Media

et al. 2014

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“…Bacchi et al ., Albert et al ., Ghedini et al ., Krishnamoorthy et al ., and Das and Pal demonstrated that the 5,5‐ or 6,5‐membered metallacycles including aryl‐C, azomethine‐N, amidate‐O or thioamidate‐S donors are formed in metalation of hydrazones derived from acid‐ or thioacid‐hydrazides. Additionally, Parbhu and Pal described the CNO and CNS pincer‐type Pd (II) complexes and their applications in Suzuki–Miyaura and Sonogashira coupling reactions, and Pandiarajan and Ramesh presented a pincer palladium (II) pyridoxal hydrazone complex as an efficient catalyst for the Suzuki–Miyaura cross‐coupling reaction (Scheme ). In contrast to palladium (II) aroylhydrazone and thiosemicarbazonate complexes, minimal attention has been paid to the palladated heterocyclic acid hydrazone derivatives .…”

Section: Introductionmentioning

confidence: 99%

ONO pincer palladium (II) complexes featuring furoylhydrazone ligands: Synthesis, characterization and catalytic activity towards Suzuki–Miyaura coupling reaction

Qian

Song

et al. 2019

Applied Organom Chemis

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Four new palladium pincer complexes incorporating ONO type furoylhydrazone ligands have been prepared in good yields. These palladium complexes were structurally characterized by elemental analysis, infrared, 1H‐ and 13C‐NMR spectra. X‐ray single crystal analyses of Pd1–Pd4 revealed that the metal center adopted a slightly distorted square planar geometry in which the hydrazone bound the metal ion via the phenolic‐O, azomethine‐N and imidolate‐O atoms. Using these ONO pincer complexes as catalyst, excellent yields of biaryls could be obtained for coupling of arylboronic acids with aryl bromides at a low catalyst loading (0.01 mol%).

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“…22 Various metal complexes of hydrazine-derived ligands have been reported with fascinating functionalities and bonding modes, potential catalysts, biologically active agents and single molecule magnets. [23][24][25][26][27][28] In acylhydrazone ligands, deprotonation of the -NH group is readily achieved, mediated by base or metal while forming complexes and is responsible for various serendipitous bonding modes. 29 Among all the complexes which we report here, metal-mediated deprotonation of -NH group is observed because it is achieved even without using any base.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural studies of half-sandwich Cp* rhodium and Cp* iridium complexes featuring mono, bi and tetradentate nitrogen and oxygen donor ligands

2017

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A series of Cp*Rh and Cp*Ir complexes of various nitrogen and oxygen donor ligands were synthesized and characterized. Mono, bi and tetradentate ligands were used to synthesize mononuclear and dinuclear complexes. Schiff base derivatives of picolinic hydrazine and 5-aminoquinoline were used in the synthesis of complexes 1-8. Among the ligands used for complexation, L1 and L2 act as bidentate, L3 as monodentate and L4 as tetradentate in forming the corresponding complexes. All the complexes were characterized by spectroscopic techniques and the structures of complexes 2, 3, 5 and 7 were unambiguously characterized by single crystal X-ray crystallography. Complexes 2 and 7 were found to have π-π stacking interactions and solvent to complex interactions, respectively. Metal-mediated deprotonation of N-H and monodentate binding of nitrogen are attributed to the formation of neutral complexes whereas ionic complexes are formed by (N,O) bonding.

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Suzuki–Miyaura cross-coupling reaction of aryl bromides catalyzed by palladium(II) pyridoxal hydrazone complexes

Cited by 36 publications

References 56 publications

A Simple Hydrophilic Palladium(II) Complex as a Highly Efficient Catalyst for Room Temperature Aerobic Suzuki Coupling Reactions in Aqueous Media

A Simple Hydrophilic Palladium(II) Complex as a Highly Efficient Catalyst for Room Temperature Aerobic Suzuki Coupling Reactions in Aqueous Media

ONO pincer palladium (II) complexes featuring furoylhydrazone ligands: Synthesis, characterization and catalytic activity towards Suzuki–Miyaura coupling reaction

Synthesis and structural studies of half-sandwich Cp* rhodium and Cp* iridium complexes featuring mono, bi and tetradentate nitrogen and oxygen donor ligands

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