Highly Efficient Method for Suzuki Reactions in Aqueous Media

Zhou, Xinglong; Guo, Xutao; Jian, Fang‐Fang; Wei, Gang

doi:10.1021/acsomega.8b00469

Cited by 18 publications

(11 citation statements)

References 26 publications

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“…Several techniques have been developed for coupling of C-C bond, which can be exemplified by Heck [17], Suzuki [18], Negishi [19], Sonogashira [20], Kumada [21], and Stille [22] coupling reactions, etc. Various metals such as palladium, rhodium, ruthenium, copper, zinc, tin, magnesium, etc [23].…”

Section: Introductionmentioning

confidence: 99%

Pd Supported IRMOF-3: Heterogeneous, Efficient and Reusable Catalyst for Heck Reaction

et al. 2019

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IRMOF-3 with a high surface area prepared by a hydrothermal method was used for deposition of Pd(OAc) 2 on IRMOF-3 particles. The final catalyst was characterized with FT-IR, nitrogen physisorption, thermogravimetry, scanning electron microscopy, transmission electron microscopy combined with energy dispersive X-ray analysis, wide angle X-ray diffraction spectroscopy and X-ray photoelectron spectroscopy. The prepared porous catalyst was effectively used in the Heck coupling reaction in the presence of an organic base. The reaction parameters such as the type of base, amounts of catalyst and solvents, temperature were optimized. The catalyst was then easily separated, washed, and reused 4 times without significant losses of catalytic activity.

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Section: Introductionmentioning

confidence: 99%

Pd Supported IRMOF-3: Heterogeneous, Efficient and Reusable Catalyst for Heck Reaction

et al. 2019

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“…Among different C–C coupling reactions, Suzuki–Miyaura is an efficient one − because handling and removal of reagents and products are easy compared to those of the corresponding compounds in organometallic reactions. − Moreover, the reaction is not affected by the number of functional groups present in aryl halides or arylboronic acids. Pd-catalyzed C–C and carbon–heteroatom coupling reactions are performed mostly by expensive, toxic, and air-sensitive P- and/or N-donating ligands like tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0) in organic solvents, and poly(2-oxazoline) palladium carbine complex in water or by in situ reduction of Pd(II) complexes. − The separation of products from these catalysts is very difficult, which seems to be the major drawback of the method.…”

Section: Introductionmentioning

confidence: 99%

Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki–Miyaura Coupling Reactions

Chatterjee

Bhattacharya

2018

ACS Omega

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Stable, catalytically active palladium nanoparticles of various average diameters (1.9–7.4 nm) have been synthesized and characterized by X-ray diffraction, spectroscopy, and microscopy techniques to demonstrate remarkable size-dependent and renewed catalytic activity toward the Suzuki–Miyaura coupling reaction in green protocol. The catalytic activity is found to depend on the amount of the reducing agent, stabilizer–precursor ratio, solvent composition, and aryl halides used. The product obtained by this reaction is characterized by 1 H NMR, 13 C NMR, and IR spectroscopy analyses. A newly developed kinetic equation illustrates that while the catalyst particles of the lowest dimension are gradually exposed to the reactants and hence activated due to partial removal of capping polymer from the catalyst surface, others are deactivated due to agglomeration during the progress of the reaction, as conformed by the microscopic profiles of the used and unused catalysts.

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“…In an additional series of reactions, bromobenzene and various dioxaborolanes were tested, and all underwent smooth coupling reactions under acidic conditions in the presence of the sydnone additive; the results are summarized in Table 5. Numerous syntheses of 22a have been reported to date, including methods starting from phenylboronic acid employing a cyclodextrin-modified Pd catalyst (100% after 4.5 h at 90 °C), 29 pepsi-type NHC Pd complexes (100% after 24 h at 22 °C), 30 and NHC-Pd magnetic nanocatalysts (99% after 30 min at 40 °C). 31 Starting from dioxaborolanes, the method described here compares favorably with the best of these approaches with respect to yield and conditions.…”

Section: Syn Thesismentioning

confidence: 99%

Suzuki–Miyaura Cross-Couplings under Acidic Conditions

Pruschinski¹,

Lücke²,

Freese³

et al. 2019

Synthesis

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Suzuki–Miyaura reactions with Pd(PPh3)4 have been carried out using lithium N-phenylsydnone-4-carboxylate as additive, which gave best yields at pH 5.7 in a mixture of acetic acid, water, and sodium carbonate. Reaction parameters such as the Pd source, the solvent, reaction time and temperature, acid, base and carboxylate have been varied and some representative examples of the Suzuki–Miyaura reaction have been examined.

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Highly Efficient Method for Suzuki Reactions in Aqueous Media

Cited by 18 publications

References 26 publications

Pd Supported IRMOF-3: Heterogeneous, Efficient and Reusable Catalyst for Heck Reaction

Pd Supported IRMOF-3: Heterogeneous, Efficient and Reusable Catalyst for Heck Reaction

Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki–Miyaura Coupling Reactions

Suzuki–Miyaura Cross-Couplings under Acidic Conditions

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