A New Highly Efficient Catalyst System for the Coupling of Nonactivated and Deactivated Aryl Chlorides with Arylboronic Acids

Zapf, Alexander; Ehrentraut, Andreas; Beller, Matthias

doi:10.1002/1521-3773(20001117)39:22<4153::aid-anie4153>3.0.co;2-t

Cited by 494 publications

(191 citation statements)

References 36 publications

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“…Normally, Suzuki reactions are carried out in a mixture of an organic solvent and an aqueous inorganic base, generally under an inert atmosphere [21,39,40]. When the reaction is performed in aqueous systems under aerobic conditions, activation by phosphine ligands is usually required [41].…”

Section: Suzuki Reaction Catalyzed By Pd-graphene Hybridsmentioning

confidence: 99%

Palladium nanoparticle-graphene hybrids as active catalysts for the Suzuki reaction

et al. 2010

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Graphene has been successfully modified with palladium nanoparticles in a facile manner by reducing palladium acetate [Pd(OAc) 2 ] in the present of sodium dodecyl sulfate (SDS), which is used as both surfactant and the reducing agent. The palladium nanoparticle-graphene hybrids (Pd-graphene hybrids) are characterized by highresolution transmission electron microscopy, atomic force microscopy, Raman spectroscopy, X-ray photoelectron spectroscopy, X-ray diffraction, and energy dispersive X-ray spectroscopy. We demonstrate that the Pd-graphene hybrids can act as an efficient catalyst for the Suzuki reaction under aqueous and aerobic conditions, with the reaction reaching completion in as little as 5 min. The influence of the preparation conditions on the catalytic activities of the hybrids is also investigated.

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Section: Suzuki Reaction Catalyzed By Pd-graphene Hybridsmentioning

confidence: 99%

Palladium nanoparticle-graphene hybrids as active catalysts for the Suzuki reaction

et al. 2010

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“…Beller et al reported a new catalyst system, with which they achieved the coupling of nonactivated and deactivated aryl chlorides highly efficiently in good yields with generally only 0.005 mol% palladium and thus under industrially viable. 21) For instance, as new efficient catalyst system, they used diadamantyl-n-butylphosphane (BuPAd 2 ) as a ligand and found that it proved to be extremely reactive. One of typical examples is shown in Eq.…”

Section: )mentioning

confidence: 99%

Organoborane coupling reactions (Suzuki coupling)

Suzuki

2004

Proc. Jpn. Acad., Ser. B

129

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“…Beller et al reported a new catalyst system, with which they achieved the coupling of nonactivated and deactivated aryl chlorides highly efficiently in good yields with generally only 0.005 mol % palladium and thus industrially useful. 21 For instance, as a new efficient catalyst system, they used diadamantyl-n-butylphosphane (P(Bu)(Ad) 2 ) as a ligand and found that it proved to be extremely reactive. In addition, the new ligands described in Scheme 3, work effectively in the coupling reaction of aromatic chlorides again.…”

Section: ç Coupling With Aromatic Chloridesmentioning

confidence: 99%

Cross-coupling Reactions of Organoboranes: An Easy Method for C–C Bonding

Suzuki¹,

Yamamoto²

2011

Chemistry Letters

153

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The palladium-catalyzed cross-coupling reaction between different types of organoboron compounds and various organic halides or triflates in the presence of base provides a powerful and general methodology for the formation of carboncarbon bonds. The Csp 2 B compounds (such as aryl-and 1-alkenylboron derivatives) and Csp 3 B compounds (alkylboron compounds) readily cross-couple with organic electrophiles to give coupled products selectively in high yields. Recently, the CspB compounds (1-alkynylboron derivatives) have been also observed to react with organic electrophiles to produce expected cross-coupled products. The overview of some of such coupling reactions is discussed here in this article. Ç IntroductionCarboncarbon bond formation reactions are important processes in chemistry, because they provide key steps in building complex, bioactive molecules developed as pharmaceuticals and agrochemicals. They are also vital in developing a new generation of ingeniously designed organic materials with novel electronic, optical, or mechanical properties, likely to play a significant role in the burgeoning area of nanotechnology.During the past 40 years, most important carboncarbon bond-forming methodologies have involved using transition metals to mediate the reactions in a controlled and selective manner. The palladium-catalyzed cross-coupling reaction between different types of organoboron compounds and various organic electrophiles including halides or triflates in the presence of base provides a powerful and general methodology for the formation of carboncarbon bonds. Here, some representatives of such reactions are shown in Scheme 1. Numbers in parentheses indicate the years first reported by our group.As one defect of the reaction, one would point out the use of bases. However, the difficulty could be overcome by using suitable solvent systems and adequate bases. Consequently, these coupling reactions have been actively utilized not only in academic laboratories but also in industrial processes. In this paper, three topics, routes to conjugated alkadienes, application to biaryls, and B-alkyl-borane coupling will be discussed. In addition, recent topics will be introduced.Such coupling reactions offer several advantages: (1) Ready availability of reactants. Cross-coupling reactions between vinylic boranes and vinylic halides were not reported to proceed smoothly in the presence of only palladium catalysts. During the initial stage of our exploration, we postulated that a drawback of the coupling is caused by the following aspects of the mechanism. The common mechanism of transition-metal-catalyzed coupling reactions of organometallic compounds with organic halides involves sequential (a) oxidative addition, (b) transmetalation, and (c) reductive elimination.1 It appeared that one of the major reasons that 1-alkenylboranes cannot react with 1-alkenyl halides is step (b). The transmetalation process between RMX (M = transition metal, X = halogen) and organoboranes does not occur readily because of the wea...

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A New Highly Efficient Catalyst System for the Coupling of Nonactivated and Deactivated Aryl Chlorides with Arylboronic Acids

Cited by 494 publications

References 36 publications

Palladium nanoparticle-graphene hybrids as active catalysts for the Suzuki reaction

Palladium nanoparticle-graphene hybrids as active catalysts for the Suzuki reaction

Organoborane coupling reactions (Suzuki coupling)

Cross-coupling Reactions of Organoboranes: An Easy Method for C–C Bonding

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