Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates

Yu, Xin; Zhang, Zhen; Song, Renyuan; Gou, Liping; Wang, Guangrong

doi:10.1515/hc-2020-0001

Cited by 11 publications

(2 citation statements)

References 35 publications

(33 reference statements)

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“…Additional references cited within the Supporting Information. [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]…”

Section: Supporting Informationmentioning

confidence: 99%

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Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole

Bakare,

Patil

2023

Eur J Org Chem

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We demonstrate the use of ligand combination approach in the Pd catalyzed direct C‐H arylation of benzothiazole and benzoxazole. The combination of two ligands phenanthroline monohydrate (Phen.H2O) and triphenylphosphine (PPh3) with Pd‐catalyst have offered the best catalytic properties in the C‐H bond arylation reactions than either of two ligands employed separately in the reactions. This protocol exhibits a wide substrate scope affording C2 arylated benzothiazole and benzoxazole derivatives in excellent yields. Mechanistic studies including kinetic isotope effect (KIE), H/D exchange and competition experiments show that the C‐H bond activation of benzothiazole/benzoxazole is very facile under reaction conditions. Furthermore, different mechanistic pathways originated from the catalytically active species such as Pd(η2‐dba)L (dba = dibenzylidene acetone) and Pd(PPh3)2 were investigated using computational methods. The computational results suggest that the generation of catalytically active species from Pd2(dba)3 is endoergic process and Phen ligand can initiate this step. On the other hand, the presence of PPh3 could be crucial for the oxidative addition of aryl halides which is the rate‐determining step of the reaction.

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“…Additional references cited within the Supporting Information. [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]…”

Section: Supporting Informationmentioning

confidence: 99%

“…The Supporting Information is available free of charge at Supporting experimental data; copies of 1 H, 13 C and 19 F NMR spectra for all products (PDF). Additional references cited within the Supporting Information [29–45] …”

Section: Supporting Informationmentioning

confidence: 99%

Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole

Bakare,

Patil

2023

Eur J Org Chem

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Synthesis and structural characterization of palladium pincer complexes: Sustainable synthesis of benzothiazoles

Anandaraj

Saranya

Ramesh

2023

Applied Organom Chemis

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An efficient Pd(II)N^N^S pincer type catalysts‐promoted sustainable construction of pharmaceutically important benzothiazole derivatives from primary alcohols and 2‐aminothiophenol via acceptorless dehydrogenative coupling (ADC) method has been described. The newly synthesized ligand L2 and the Pd(II) complexes in addition to L1 and L3 were characterized by analytical and Fourier transform infrared spectroscopy (FT‐IR), UV–visible (UV–vis), and nuclear magnetic resonance (NMR) spectral techniques. Further, the ORTEP views of the complexes 2 and 3 were established by a single crystal XRD study, which evidenced the coordination of the thiosemicarbazone ligands and disclose the square‐planar geometry around the Pd(II) ion. The present homogeneous catalytic system involves synthesizing a range of benzothiazoles via C−S and C−N bond formation with excellent yields up to 93%. The described methodology employs a sustainable, highly abundant, and inexpensive alcohol as starting material using 1 mol% catalyst loading, and water and hydrogen gas are the only by‐products. Furthermore, a plausible mechanism involving in situ aldehyde formation via dehydrogenation of primary alcohols has been proposed. A large‐scale synthesis of 2‐(4‐methoxyphenyl)benzo[d]thiazole illustrates the synthetic utility of the present catalytic protocol.

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PolyVinyl alcohol and copper nickel co‐doped titania nanocomposite: Designing, characterization, optical properties, and catalytic application in the synthesis of aryl derivatives of benzothiazole and benzimidazole

Mahajan,

Gupta

2023

Applied Organom Chemis

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The paper examines the properties and potential applications of a nanocomposite material composed of polyvinyl alcohol (PVA) and copper nickel co‐doped titanium dioxide (Cu‐TiO2‐Ni). The material was synthesized using a simple precipitation process, and its properties were characterized using various analytical techniques, including powder X‐ray diffraction, Fourier transform infrared spectroscopy, thermogravimetry analysis, field emission scanning electron microscopy, and high‐resolution tunnelling electron microscopy; Brunauer–Emmett–Teller (BET) surface area was investigated. The results showed that the addition of Cu‐TiO2‐Ni to PVA improved the material's Ultraviolet–visible spectroscopy (UV) absorption properties. Additionally, the PVA/Cu‐TiO2‐Ni nanocomposite material exhibited potential for use in a range of applications, including catalysis. Its utility in synthesizing aryl derivatives of benzothiazole and benzimidazoles, which are crucial intermediates in the fine chemical, agrochemical, and pharmaceutical industries and material science, was evaluated. It was found to offer several advantages, including a quick reaction time, simple workup, and good to excellent isolated yields. These characteristics make this protocol both practical and economically intriguing.

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Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates

Cited by 11 publications

References 35 publications

Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole

Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole

Synthesis and structural characterization of palladium pincer complexes: Sustainable synthesis of benzothiazoles

PolyVinyl alcohol and copper nickel co‐doped titania nanocomposite: Designing, characterization, optical properties, and catalytic application in the synthesis of aryl derivatives of benzothiazole and benzimidazole

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