Pd/C as a Highly Active Catalyst for Heck, Suzuki and Sonogashira Reactions

Heidenreich, Roland G.; Köhler, Klaus; Krauter, Jürgen G.E.; Pietsch, Jörg

doi:10.1055/s-2002-32589

Cited by 198 publications

(100 citation statements)

References 1 publication

(2 reference statements)

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“…[110][111][112][113] Although many efforts to prepare solid-phase catalysts for the Heck reaction have been made, homogeneous catalytic systems have advantages on catalytic activity. [114][115][116][117][118][119][120][121][122] In fact, it was known that designing recyclable system for the Heck reaction was more challenging than that for the Suzuki-Miyaura reaction. These catalysts were less stable under the Heck reaction condition, and thus often decompose physically or chemically.…”

Section: Development Of a Novelmentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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IntroductionDevelopment of immobilized and insoluble metal catalysts is of great interest in recent organic chemistry. [1][2][3][4][5][6][7][8][9] The simple recovery of catalysts by filtration and their reuses resulted in enhancing the economical evaluation of the reaction. At the same time, there is a prospect that the environmental pollution caused by residual metals in the waste fluid will be decreased. Although a great deal of effort has been made to carry out such ideal reactions using immobilized metal catalysts, what seems to be lacking is the efficiency of the catalytic systems. It is obvious that the heterogeneous catalytic systems exhibit generally lower activity than the homogeneous ones. Besides, it is expected that the activity of the catalysts decreases gradually in the recycled systems because the metal species leaches away from their supports. Taking these into consideration, we decided to concentrate on developing insoluble metal catalysts which are highly active and stable. We designed that they were still effective in the use of ppm mol eq, and in the recycled use of many times in any reaction media. To achieve the challenging theme, we have focused on the amphiphilic insoluble catalysts based on a novel concept (Chart 1).Over the past few decades, a considerable numbers of study have been made on solid-phase catalysts which were immobilized with cross-linked polystyrene resins, silica gels or metals. These catalytic systems, however, generally resulted in lower catalytic activity compared with their soluble counterparts, and were often obliged to use hazardous chlorohydrocarbon solvents. [10][11][12][13][14][15] Besides, reuse of these catalysts was often difficult owing to the gradual decline of the catalytic activity. These problems made them less practical.In traditional triphase catalysts, as I have mentioned before, a catalytic species was anchored to a linker that was immobilized to a polymer resin or silica gel (Chart 1, above). In July 2005Chem. Pharm. Bull. 53(7) 723-739 (2005)

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Section: Development Of a Novelmentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…However, these reactions were performed at high Pd concentrations (5 mol%) and over long reaction times (24 h). The results of Köhler and co-workers also exhibited the activity of Pd/C for the SM reaction of 4-chloroacetophenone at relatively low Pd concentrations (0.05-0.25 mol%) in an NMP/water mixture (10:3) at 120 • C [73]. Pd/C was also demonstrated to be an active catalyst for the SM reactions of aryl chlorides in water [74].…”

Section: Suzuki-miyaura Reactions Of Aryl Chloridesmentioning

confidence: 87%

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki–Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

Durgun

Aksın

Artok

2007

Journal of Molecular Catalysis A: Chemical

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The Pd(NH 3 ) 4 2+ -loaded NaY zeolite was found to be a highly active catalyst precursor for Suzuki-Miyaura (SM) reactions of aryl bromides and aryl chlorides at low Pd concentrations in air. Aryl bromides and arylboronic acids can couple effectively both in pure water and in N,Ndimethylacetamide/water mixtures (1/1) within minutes with turnover frequencies (TOF) up to 4 × 10 5 h −1 . The presence of a minute amount of water was crucial for the success of the reaction with chloroarenes. The excess amounts of as-received zeolite provided the necessary water for the reaction. The results suggest that the combined use of the water-zeolite system may have a synergistic effect in the reaction.

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“…167 Some other interesting results about Suzuki cross-coupling reactions catalysed by Pd on carbon have been described. 135,[169][170][171] For instance, this heterogeneous catalyst proved to be able to catalyse the Suzuki reaction with aryl chlorides at 80°C in a 20:1 mixture of dimethylacetamide and water, in the presence of K 2 CO 3 as the base. 170 The ability of heterogeneous Pd to activate the C-Cl bond was explained in terms of a synergistic anchimeric and electronic effect that occurs between the Pd surface and the aryl chloride.…”

Section: Scheme 12mentioning

confidence: 99%

“…E 105 CA/ W 5% Pd, product of Degussa AG) was demonstrated to be a highly active (TON up to 36,000), selective and heterogeneous catalyst for cross-couplings of phenylboronic acid with aryl bromides or activated aryl chlorides. 171 This catalyst allowed very low palladium concentrations (0.005 mol%) and high conversions of aryl bromides within a few hours. 171 In recent years, palladium nanoparticles have also been used as catalysts for Suzuki reactions.…”

Section: Scheme 12mentioning

confidence: 99%

“…171 This catalyst allowed very low palladium concentrations (0.005 mol%) and high conversions of aryl bromides within a few hours. 171 In recent years, palladium nanoparticles have also been used as catalysts for Suzuki reactions. [172][173][174] In fact, these particles have a characteristicly high surface-to-volume ratio and, consequently, a large fraction of the palladium atoms are at the surface and available for catalysis.…”

Section: Scheme 12mentioning

confidence: 99%

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2004

Synthesis

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This review with 206 references covers the literature published until March 2004 on the development and applications of new efficient catalyst systems for the Suzuki palladium-catalysed cross-coupling reaction of organoboron compounds with organic electrophiles. Where possible, the relative advantages of the new catalyst systems in this synthetically very important carbon-carbon bond forming reaction have been compared.

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Pd/C as a Highly Active Catalyst for Heck, Suzuki and Sonogashira Reactions

Cited by 198 publications

References 1 publication

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki–Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

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