Molten Salts as an Efficient Medium for Palladium Catalyzed C-C Coupling Reactions

Kaufmann, Dieter; Nouroozian, Mahmoud; Henze, Heiko

doi:10.1055/s-1996-5658

Cited by 160 publications

(75 citation statements)

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“…The Heck reaction has been carried out in tetraalkylammonium and phosphonium bromide molten salts [11] with good yields, and with the catalyst being used again for at least two more runs. However the use of this type of molten salt as a replacement for common solvents is unlikely to come about.…”

Section: Introductionmentioning

confidence: 99%

Moisture Stable Ambient Temperature Ionic Liquids: Solvents for the New Millennium. 1. The Heck Reaction

Howarth

Dallas

2000

Molecules

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Section: Introductionmentioning

confidence: 99%

Moisture Stable Ambient Temperature Ionic Liquids: Solvents for the New Millennium. 1. The Heck Reaction

Howarth

Dallas

2000

Molecules

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“…The Heck cross-coupling reaction is a common reaction for the formation of carbon-carbon bonds between alkenes and organic halides (Heck & Nolley, 1972). Kaufmann et al (1996) applied a phosphonium-based IL, trihexyl(tetradecylphosphonium) bromide ([P 6,6,6,14 ][Br], trade name Cyphos ® IL 162) as recyclable medium for the palladium-mediated Heck coupling of aryl halides with acrylate esters (see Figure 7) for the first time. Although relatively high yields were obtained, the reaction temperature was rather high (100°C) and more activated aryl halides were strongly favored.…”

Section: Applications As Catalysts and Solvents In Organic Synthesismentioning

confidence: 99%

Quaternary Ammonium and Phosphonium Ionic Liquids in Chemical and Environmental Engineering

Stojanovic¹,

Morgenbesser²,

Kogelnig³

et al. 2011

Ionic Liquids: Theory, Properties, New Approaches

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“…[14][15][16][17][18][19][20] Multiphase conditions. The effect of A336 on the Heck coupling was then investigated in the multiphase system.…”

Section: Chemoselectivitymentioning

confidence: 99%

Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

et al. 2004

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The rate of the Pd/C catalyzed Heck coupling of Ar-I with CH 2 CH-R is accelerated tenfold by the presence of Aliquat 336 (A336), a well known phase transfer catalyst, and an ionic liquid. Both when conducted in A336 as solvent, and in an isooctane/A336/aqueous triphasic mixture, the Heck reaction of aryl iodides with electron deficient olefins, catalyzed by Pd/C, proceeds with high yields and selectivity. When KOH is used instead of Et 3 N, selective formation of the biphenyl rather than the Heck product, is observed. Aryl bromides react more sluggishly, and only the more activated ones undergo the Heck reaction. In the absence of the olefin, aryl halides possessing an electron withdrawing group are reduced to the corresponding Ar-H.

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Molten Salts as an Efficient Medium for Palladium Catalyzed C-C Coupling Reactions

Cited by 160 publications

References 0 publications

Moisture Stable Ambient Temperature Ionic Liquids: Solvents for the New Millennium. 1. The Heck Reaction

Moisture Stable Ambient Temperature Ionic Liquids: Solvents for the New Millennium. 1. The Heck Reaction

Quaternary Ammonium and Phosphonium Ionic Liquids in Chemical and Environmental Engineering

Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

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