P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Wong, Siu Wai; So, Chau Ming; Chung, Kin Ho; Luk, Chi Him; Lau, Chak Po; Kwong, Fuk Yee

doi:10.1016/j.tetlet.2012.05.017

Cited by 22 publications

(5 citation statements)

References 57 publications

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“…In the same year, Kwong et al synthesized a hemilabile phosphine ligand which stabilized the Pd catalyst and promoted oxidative addition. The ligands containing N and P reduced the amount of catalyst down to 1-500 ppm (Scheme 1b) [6,7]. The multidentate phosphine ligand promoted Sonogashira coupling reactions in water under 1-500 ppm Pd (Scheme 1c) [8,9].…”

Section: Introductionmentioning

confidence: 99%

α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

Guo

Wei

Yang³

et al. 2020

Catalysts

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In the palladium-catalyzed C−C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one (L2) as the ligand, catalyst loading was reduced to 5-10 ppm. In this newly developed catalytic system, a variety of (hetero)arene iodines and alkynes could be tolerated, resulting in good yields of the corresponding cross-coupling products.

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Section: Introductionmentioning

confidence: 99%

α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

Guo

Wei

Yang³

et al. 2020

Catalysts

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“…Accordingly, thousands of Pd catalysts with various ligand systems have been gradually developed to revolutionize this field. Homogenous categories are primarily exploited and widely employed, including phosphane-based ligands such as tertiary-, hemilable-, biophenyl-, and indole-types , and nitrogen-containing ligands like N-heterocyclic carbenes, amines, oximes, and Schiff bases. − Although this kind of catalyst is usually highly active, a major problem is the difficulty in their recovery and recycling. By comparison, many novel heterogeneous nanoparticles Pd catalysts have been designed in recent years by immobilizing Pd complexes on various supports like mesoporous silica, zeolites, carbon, and metal–organic frameworks (MOFs). , The use of these catalysts facilitates the SMC chemistry process and achieves the efficient utilization of the increasingly expensive Pd metal.…”

Section: Introductionmentioning

confidence: 99%

“…2 Accordingly, thousands of Pd catalysts with various ligand systems have been gradually developed to revolutionize this field. Homogenous categories are primarily exploited and widely employed, including phosphane-based ligands such as tertiary-, hemilable-, biophenyl-, and indole-types 9,10 and nitrogen-containing ligands like N-heterocyclic carbenes, amines, oximes, and Schiff bases. 11−14 Although this kind of catalyst is usually highly active, a major problem is the difficulty in their recovery and recycling.…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles on Covalent Organic Framework Supports as Catalysts for Suzuki–Miyaura Cross-Coupling Reactions

Liu

Zhan

Wang

et al. 2021

ACS Appl. Nano Mater.

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Suzuki–Miyaura cross-coupling (SMC) reaction by palladium (Pd) catalysis is widely used in cross-coupling chemistry synthesis for CC bond formation, yet the biaryl products are generally lacking halo substituents due to highly active palladium species. Suitable catalysts according to this property for the region-selective SMC synthesis of biaryl derivatives with halo substituents did not receive due and sufficient attention. Here, we report the facile synthesis of a covalent organic frameworks (COFs)-supported nanoparticles Pd catalyst that can region-selectively catalyze the SMC reaction of aryl boronic acids and aryl halides, especially with halogenated aryl boronic acids. The methodology exhibits mild operating conditions, broad functional group tolerance, and environmental friendliness and can be strategically applied for cross-coupling scenarios governed by sequential transition metal catalysts to build with or without a halo-substituted moiety. The Pd/COF-SMC nanoparticles catalysts are stable and reusable and succeed in synthesizing halo-substituted biaryl products in excellent yield, which avoids the homocoupling of halogenated aryl boronic acid. The most outstanding advantage is the precise regulation of nanoparticles Pd activity with the well-designed COF ligand.

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“…Moreover, potassium organotrifluoroborates showed good resistances to either protodeboronations or self‐coupling reactions and could understand lots of reaction conditions used in routine organic synthesis. Although there have been several catalytic systems for the Suzuki‐Miyaura coupling reactions of potassium aryltrifluoroborates with heteroaryl halides using N ‐containing ligands and heterogeneous catalysts, few attention has been paid to develop ligand‐free catalytic systems in aqueous systems. Molander's group reported the first ligand‐free Pd (OAc) 2 catalyzed Suzuki‐Miyaura couplings of potassium organotrifluoroborates with heteroaryl bromides .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of heterobiaryls via Suzuki‐Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems

Liu

Zhao

et al. 2019

Applied Organom Chemis

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A variety of heterobiaryl compounds have been synthesized by the Suzuki‐Miyaura coupling reactions of heteroaryl halides with potassium aryltrifluoroborates. Pd (OAc)2 was found to be highly efficient for the Suzuki‐Miyaura coupling reactions of various heteroaryl halides with potassium aryltrifluoroborates in aqueous systems, delivering the corresponding heterobiaryl compounds in good to excellent yields.

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P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Cited by 22 publications

References 57 publications

α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

Palladium Nanoparticles on Covalent Organic Framework Supports as Catalysts for Suzuki–Miyaura Cross-Coupling Reactions

Synthesis of heterobiaryls via Suzuki‐Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems

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