Synthesis and palladium(II) metal chemistry of thiazoline/imidazoline derived ligands: An efficient catalyst for cross-coupling reactions of arylboronic acids with acid chlorides and aryl halides

Sudharsan, Murugesan; Suresh, D.

doi:10.1016/j.ica.2018.09.012

Cited by 10 publications

(11 citation statements)

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“…Encapsulation of Pd nanoparticles (NPs) within the thiazoline bridged periodic mesoporous organosilica was achieved via three different stages. Initially, the reaction of 2‐aminobenzonitrile ( 1 ) with cysteamine hydrochloride in equimolar reaction under solvent‐free condition afforded good yields of 2‐(4,5‐dihydrothiazol‐2‐yl)aniline ( 2 ) . Subsequent reaction of 2 with (3‐isocyanatopropyl)triethoxysilane in 1 : 1 molar ratio under refluxing condition in toluene produced the thiazoline‐silyl precursor 3 as yellow powder in 95% of yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Initially, the reaction of 2-aminobenzonitrile (1) with cysteamine hydrochloride in equimolar reaction under solvent-free condition afforded good yields of 2-(4,5dihydrothiazol-2-yl)aniline (2). [46] Subsequent reaction of 2 with (3-isocyanatopropyl)triethoxysilane in 1 : 1 molar ratio under refluxing condition in toluene produced the thiazoline-silyl precursor 3 as yellow powder in 95% of yield (Scheme 1). The compounds 2 and 3 were characterized through 1 H and 13 CN MR spectroscopy.…”

Section: Synthesis Of Tpmo and Pd-tpmomentioning

confidence: 99%

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Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & C_sp²−C_sp² Bond Formation Reactions

et al. 2020

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Thiazoline functionalized periodic mesoporous organosilica (TPMO) supported palladium nanoparticles (Pd-TPMO) were fabricated through a co-condensation approach and successive incorporation of palladium nanoparticles using a doublesolvent technique. The TPMO and Pd-TPMO were characterized through 29 Si MAS NMR, FTIR, SAXS, XPS, FESEM, TEM and N 2 adsorption-desorption, which revealed the morphological and physicochemical properties of the materials. The catalytic performance of Pd-TPMO was evaluated for hydrogenation of industrially important compounds and C sp 2 À C sp 2 bond-formation reactions. The Pd-TPMO mediated catalytic reactions were found to be effective in producing the corresponding products with excellent yields and selectivity. The size and stability of palladium nanoparticles within the confined organosilica framework promotes excellent activity and recyclability of the catalyst without a significant loss in the yields for hydrogenation and C sp 2 À C sp 2 bond-formation reactions.[a] Dr.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Tpmo and Pd-tpmomentioning

confidence: 99%

Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & C_sp²−C_sp² Bond Formation Reactions

et al. 2020

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“…[(C 3 H 4 NS)(1,2-C 6 H 4 ) NH 2 ] (1) was prepared according to the literature method. [65] The nuclear magnetic resonance (NMR) spectra were recorded in deuterated solvents at room temperature on a Bruker Avance 300 ( 1 H and 13 C) spectrometer operating at 300 MHz for 1 H and 75 MHz for 13 C. Deuterated solvents were dried by storage over 4 Å molecular sieves. Chemical shifts (δ) are expressed in ppm using TMS as internal standard and coupling constants (J) are given in Hz.…”

Section: Methodsmentioning

confidence: 99%

“…First, [(C 3 H 4 NS)(1,2-C 6 H 4 )NH 2 ] (1) was prepared by the condensation reaction between 2-aminobenzonitrile, cysteamine hydrochloride and sodium hydroxide under neat reaction condition. [65] Treatment of 1 with picolinic acid and N- The perspective view of molecular structure of ligand 2 with the atomic numbering is given in figure 2 along with its selected geometrical parameters (in the caption). The details of the crystal structure determinations are given in Table 1.…”

Section: Synthesis and Characterization Of Ligand (2)mentioning

confidence: 99%

Heteroleptic Palladium(II) Complexes of Thiazolinyl‐picolinamide Derived N^∩N^∩N Pincer Ligand: An Efficient Catalyst for Acylative Suzuki Coupling Reactions

et al. 2021

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Synthesis, reactivity, characterization, and catalytic activities of a series of palladium(II) complexes containing the thiazolinyl-picolinamide derived pincer ligand is reported. Treatment of 2-aminobenzonitrile with cysteamine and subsequent treatment with 2-picolinic acid afforded the thiazolinyl-picolinamide derived tridentate pincer ligand N \ N \ N (2). Treatment of 2 either with (COD)PdCl 2 or PdCl 2 in 1 : 1 ratio afforded the palladium(II) complex [(k 3 -N \ N \ N)PdCl] (3). A reaction between Pd(OAc) 2 and 2 in equimolar ratio in dichloromethane gave [(k 3 -N \ N \ N)Pd(η 1 -OAc)] (4) which on further treatment with triflic acid in acetonitrile produced the [(k 3 -N \ N \ N)Pd(N�CÀ CH 3 )]OTf (5). The complex 5 was further treated with auxiliary ligands to produce the cationic heteroleptic palladium complexes, [(k 3 -N \ N \ N)Pd(NC 5 H 5 )]OTf (6), [(k 3 -N \ N \ N)Pd(NC 5 H 4 CN)]OTf (7), and [(k 3 -N \ N \ N) Pd(NC 5 H 4 NMe 2 )]OTf (8), respectively. The newly synthesized compounds were characterized by 1 H and 13 C{ 1 H} NMR spectroscopic techniques and the molecular structures of 2-4, 6 and 8 were established. The catalytic activity of palladium(II) complexes (3-8) were evaluated for the acylative Suzuki coupling reaction between aryl carboxylic acids and arylboronic acids to yield unsymmetrically substituted biaryl ketones. The effect of reaction conditions viz., solvent, base, temperature, catalyst loading were evaluated, and complex 4 was found to be an excellent catalyst with a maximum TOF of 19.8 min À 1 .

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“…13 1-Phenylnaphthalene (3i, 194 mg). 24 1 H NMR (400 MHz, CDCl 3 ): δ 7.89 (t, J = 7.0 Hz, Ar−H, 2H), 7.83 (d, J = 8.2 Hz, Ar− H, 1H), 7.53−7.36 (m, Ar−H, 9H). 13 C NMR (101 MHz, CDCl 3 ): δ 140.7, 140.2, 133.8, 131.6, 130.0, 128.2, 127.6, 127.2, 126.9, 126.0, 125.7, 125.3.…”

Section: General Procedures For the Synthesis Of Imidazolium Saltmentioning

confidence: 99%

N-Heterocarbene Palladium Complexes with Dianisole Backbones: Synthesis, Structure, and Catalysis

et al. 2019

Organometallics

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A series of palladium N-heterocyclic carbenes (NHCs), complexes C1–C5, bearing dianisole backbones and substituted N-aryl moieties have been synthesized and characterized. The electronic effect as well as the steric environment of the NHC ligands has been assessed. The synthesized palladium complexes were applied for Suzuki–Miyaura cross-coupling reactions under aerobic conditions. The relationship between the catalytic structure and catalytic performance was then extensively investigated. Upon optimizing the reaction conditions, the C4 was found to be highly efficient to catalyze the cross-coupling of (hetero)aryl chlorides with (hetero)arylboronic acids at a 0.1 mol % palladium loading.

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Synthesis and palladium(II) metal chemistry of thiazoline/imidazoline derived ligands: An efficient catalyst for cross-coupling reactions of arylboronic acids with acid chlorides and aryl halides

Cited by 10 publications

References 47 publications

Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & C_sp²−C_sp² Bond Formation Reactions

Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & C_sp²−C_sp² Bond Formation Reactions

Heteroleptic Palladium(II) Complexes of Thiazolinyl‐picolinamide Derived N^∩N^∩N Pincer Ligand: An Efficient Catalyst for Acylative Suzuki Coupling Reactions

N-Heterocarbene Palladium Complexes with Dianisole Backbones: Synthesis, Structure, and Catalysis

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Synthesis and palladium(II) metal chemistry of thiazoline/imidazoline derived ligands: An efficient catalyst for cross-coupling reactions of arylboronic acids with acid chlorides and aryl halides

Cited by 10 publications

References 47 publications

Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & Csp2−Csp2 Bond Formation Reactions

Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & Csp2−Csp2 Bond Formation Reactions

Heteroleptic Palladium(II) Complexes of Thiazolinyl‐picolinamide Derived N∩N∩N Pincer Ligand: An Efficient Catalyst for Acylative Suzuki Coupling Reactions

N-Heterocarbene Palladium Complexes with Dianisole Backbones: Synthesis, Structure, and Catalysis

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Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & C_sp²−C_sp² Bond Formation Reactions

Palladium Nanoparticles Incorporated Thiazoline Functionalized Periodic Mesoporous Organosilica: Efficient Catalyst for Selective Hydrogenation & C_sp²−C_sp² Bond Formation Reactions

Heteroleptic Palladium(II) Complexes of Thiazolinyl‐picolinamide Derived N^∩N^∩N Pincer Ligand: An Efficient Catalyst for Acylative Suzuki Coupling Reactions