Palladium catalysed heck reactions and allylic substitution reactions using glass bead technology

Tonks, Louise; Anson, M.; Hellgardt, Klaus; Mirza, Amin; Thompson, David F.; Williams, Jonathan M. J.

doi:10.1016/s0040-4039(97)00890-3

Cited by 62 publications

(18 citation statements)

References 6 publications

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“…24 Thus, bromobenzene 28 and bromoiodobenzene 29 also underwent coupling reactions with methyl acrylate to produce the cinnamate products 27 and 30 in moderate yields with low levels of palladium leaching (Scheme 10). The coupling of iodobenzene 25 with the allylic alcohol 31 afforded the ketone 32.…”

Section: Palladium Catalysed Heck Reactionsmentioning

confidence: 99%

Transition metal catalysed reactions using glass bead technology

Anson¹,

Leese²,

Tonks³

et al. 1998

J. Chem. Soc., Dalton Trans.

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A successful method for rendering homogeneous transition metal catalysts heterogeneous has emerged from glass bead technology. The process generally combines high activity and selectivity with facile recyclability. Glass bead technology, and related approaches, have been applied to a wide range of reactions with results paralleling, and sometimes exceeding, those obtained from their homogeneous counterparts. Outlined is the current scope of this research, with an emphasis on work on supported palladium reagents. A novel approach for the retrieval of precious metals from reaction mixtures stemming from these studies is also outlined.

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Section: Palladium Catalysed Heck Reactionsmentioning

confidence: 99%

Transition metal catalysed reactions using glass bead technology

Anson¹,

Leese²,

Tonks³

et al. 1998

J. Chem. Soc., Dalton Trans.

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“…It is peculiar that the technology was renamed 'glass bead technology' in a review on the topic. 23 The investigated reactions range from hydroformylation, to hydrogenation, Wacker oxidation, Heck couplings, 24 Suzuki couplings, allylic substitution; using Rh, Pd, Co, Pt; and in the presence of supported phases, water, PEGs, ethylene glycol.…”

Section: Supported Liquid Phasesmentioning

confidence: 99%

Multiphasic Heterogeneous Catalysis Mediated by Catalyst‐Philic Liquid Phases

Tundo

Perosa

2007

ChemInform

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This critical review addresses heterogeneous catalysis in systems where multiple liquid phases coexist and where one of the phases is catalyst-philic. This technique provides built-in catalyst separation, and product recovery for organic reactions. Focus is placed on the components of the multiphasic systems with emphasis on the constituents of the catalyst-philic phases (PEGs, onium salts, ionic liquids) that incorporate the catalysts, as well as on the effects on catalytic efficiency. It collects a wide body of scattered information that is often labelled with different terms.

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“…The reaction performed with 4-bromoacetophenone, 4-bromobenzaldehyde, 4-trifluoromethylbromobenzene or 4-fluorobromobenzene also proceed in good yield using 0.01% catalyst (Table 1, entries 2, 3 and 6-10). The coupling using the ortho-substituted aryl bromides 2-trifluoromethylbromobenzene, 2-fluorobromobenzene or 2-methylbromobenzene gave similar or higher TONs of 33 000, 67 000 and 7500 than the para-substituted aryl bromides (Table 1, entries [17][18][19][20][21][22]. The di-ortho-substituted 2,6-difluorobromobenzene was also reacted using 0.01% catalyst (Table 1, entry 25).…”

Section: Introductionmentioning

confidence: 99%

Heck reactions of aryl halides with alk‐1‐en‐3‐ol derivatives catalysed by a tetraphosphine–palladium complex

Berthiol

Doucet

Santelli

2006

Applied Organom Chemis

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cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane-[PdCl(C 3 H 5 )] 2 efficiently catalyses the Heck reaction of alk-1-en-3-ol with a variety of aryl halides. In the presence of hex-1-en-3-ol or oct-1-en-3-ol, the β-arylated carbonyl compounds were selectively obtained. Turnover numbers up to 84 000 can be obtained for this reaction. Linalool and 2-methylbut-3-en-2-ol led regio-and stereoselectively to the corresponding (E)-1-arylalk-1-en-3-ol derivatives. A minor electronic effect of the substituents of the aryl bromide was observed. Quite similar reaction rates were generally observed in the presence of activated aryl bromides such as bromoacetophenone and deactivated aryl bromides such as bromoanisole, indicating that, with these alkenols and this catalyst, the oxidative addition of aryl bromides to palladium is not the rate-limiting step. It should be noted that this reaction also proceeds with sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6-triisopropylbromobenzene or with a vinyl bromide. On the other hand, low yields were obtained with aryl chlorides.

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Palladium catalysed heck reactions and allylic substitution reactions using glass bead technology

Cited by 62 publications

References 6 publications

Transition metal catalysed reactions using glass bead technology

Transition metal catalysed reactions using glass bead technology

Multiphasic Heterogeneous Catalysis Mediated by Catalyst‐Philic Liquid Phases

Heck reactions of aryl halides with alk‐1‐en‐3‐ol derivatives catalysed by a tetraphosphine–palladium complex

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