Polyethylene-bound soluble recoverable palladium(0) catalysts

Bergbreiter, David E.; Weatherford, David A.

doi:10.1021/jo00272a050

Cited by 84 publications

(33 citation statements)

References 4 publications

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“…After completion of the reaction catalyst recovery can be obtained by cooling to ambient temperature and phase separation. [35][36][37][38][39] In a modification of this concept, the polymerbased catalyst is used together with water and the organic substrates. Under these conditions the catalyst is insoluble in both phases at room temperature.…”

Section: Thermoregulated Phase-transfer Catalystsmentioning

confidence: 99%

Thermoregulated Liquid/Liquid Catalyst Separation and Recycling

2006

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Considerable effort has been done to overcome the loss of catalyst in homogeneously catalysed processes. In this contribution we describe five recycling concepts for thermoregulated catalyst separation and recycling: fluorous biphasic systems (FBS), thermoregulated phase transfer catalysis (TRPTC), soluble polymer-based catalysis, thermoregulated microemulsions and temperature-dependent multicomponent solvent systems (TMS). Each of these concepts has its own special advantages like low catalyst leaching or simple process engineering but also drawbacks like usage of expensive special solvents or complex and expensive catalysts. In this context, TMS systems exhibit most advantages of the other concepts combined with the possibility to use common and cheap solvents as well as numerous classical molecular catalysts. Therefore, TMS systems are expected to be one of the most promising thermomorphic recycling concepts for industrial scale.

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Section: Thermoregulated Phase-transfer Catalystsmentioning

confidence: 99%

Thermoregulated Liquid/Liquid Catalyst Separation and Recycling

2006

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“…A diphenylphosphine-terminated ethylene oligomer has been used as a ligand for palladium (0) and palladium (II). 108 This polymer is soluble at 100ЊC in toluene, and successfully catalyzed reactions typically catalyzed by (Ph 3 P) 4 Pd and (Ph 3 P) 2 Pd(OAc) 2 . For example, allylic esters could be cleanly displaced by secondary amines, to give the tertiary amine product (Table XLVI).…”

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confidence: 99%

Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

139

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The current interest in solid-phase organic synthesis has led to a renewed interest in a complementary technique in which solid supported reagents are used in solution phase chemistry. This technique obviates the need for attachment of the substrate to a solid-support, and enables the chemist to monitor the reactions using familiar analytical techniques. The purpose of this review is to increase awareness of the wide range of useful transformations which can be accomplished using solid-supported reagents.

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“…With piperidine the reaction started slowly at -20°C, and after 1 h around 10 % of the allylation product could be determined. [19] After 1 h at 0°C the level of conversion was ca. 45 % and after a further 1 h at room temperature it was complete (Entry 1).…”

Section: Resultsmentioning

confidence: 99%

Insights into the Reaction Behaviour of Stannylated Allylic Substrates

2010

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Stannylated allylic substrates are versatile building blocks for organic synthesis. Pd0‐catalysed coupling reactions of 2‐stannylated allylic carbonates, acetates and phenoxides with amines, malonates, phenoxides, imides and distannanes provide the corresponding substituted allylic compounds, which are suitable for subsequent modifications including Stille coupling reactions. The reaction mechanisms are dependent on the temperature and the nucleophiles used. Tsuji–Trost allylic substitution takes place with organic nucleophiles at low temperature. When distannane is employed at higher temperature, on the other hand, Pd0‐catalysed bismetallation of allenes formed in situ by elimination of tributyltin methoxide predominates.

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Polyethylene-bound soluble recoverable palladium(0) catalysts

Cited by 84 publications

References 4 publications

Thermoregulated Liquid/Liquid Catalyst Separation and Recycling

Thermoregulated Liquid/Liquid Catalyst Separation and Recycling

Solid-supported reagents in organic synthesis

Insights into the Reaction Behaviour of Stannylated Allylic Substrates

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