Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium

LeBlond, Carl; Andrews, A. Abraham Eben; Sun, Yuhang; Sowa, John R.

doi:10.1021/ol015850d

Cited by 283 publications

(142 citation statements)

References 31 publications

Supporting

Mentioning

140

Contrasting

Unclassified

Order By: Relevance

“…The catalytic activity of PdAS for the heterogeneous Suzuki-Miyaura reaction [76][77][78][79][80][81][82][83][84][85][86][87][88][89] was investigated (Table 5). Since "water" is the most safe, non-toxic, and easily available solvent, numerous attempts have been made in utilizing it to the organic reactions.…”

Section: Catalytic Activity Of Pdas For the Suzukimiyaura Reactionmentioning

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

View full text Add to dashboard Cite

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)

show abstract

Section: Catalytic Activity Of Pdas For the Suzukimiyaura Reactionmentioning

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

View full text Add to dashboard Cite

show abstract

“…It was demonstrated that a Pd/C catalyzed Suzuki crosscoupling reactions of activated chloroarenes with various arylboronic acids were possible upon fine adjustment of the DMA/water ratio [72]. However, these reactions were performed at high Pd concentrations (5 mol%) and over long reaction times (24 h).…”

Section: Suzuki-miyaura Reactions Of Aryl Chloridesmentioning

confidence: 99%

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

View full text Add to dashboard Cite

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.

show abstract

“…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%

“…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. 170 On the other hand, a specially optimised air-stable Pd on activated carbon catalyst (i.e. 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.…”

Section: Scheme 12mentioning

confidence: 99%

Untitled

2004

Synthesis

View full text Add to dashboard Cite

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.

show abstract

Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium

Cited by 283 publications

References 31 publications

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

Untitled

Contact Info

Product

Resources

About