Palladium-Catalyzed Head-to-Head Telomerization of Isoprene with Amines

and, Susan M. Maddock†; Finn, M. G.

doi:10.1021/om000286g

Cited by 55 publications

(38 citation statements)

References 27 publications

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“…[a] [113] Ligand Precursor [a] T = RT, t = 40 h, 0.5 mol % Pd based on isoprene, n Pd :n P 1:1 [b] See Scheme 3. [a] T = 100 8C, t = 32 h, acetonitrile, n Pd 0.375 mmol, n aniline /n iso.…”

Section: Telomerization Of Isoprene With Aminesmentioning

confidence: 99%

Telomerization: Advances and Applications of a Versatile Reaction

et al. 2009

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The transition-metal catalyzed telomerization of 1,3-dienes with different nucleophiles leads to the synthesis of numerous products, such as sugar ethers, substituted lactones, or terpene derivatives, which can be applied in the cosmetic and pharmaceutical industry as well as in polymers and flavors. The reaction can be controlled by the choice of the catalytic system, the feedstock, and the reaction conditions. Since telomerization was developed in 1967, there have been many efforts to utilize this reaction. Herein we give an overview of the versatility of telomerization based on examples from research and industry, particular emphasis is placed on catalyst and process development as well as mechanistic aspects.

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“…[a] [113] Ligand Precursor [a] T = RT, t = 40 h, 0.5 mol % Pd based on isoprene, n Pd :n P 1:1 [b] See Scheme 3. [a] T = 100 8C, t = 32 h, acetonitrile, n Pd 0.375 mmol, n aniline /n iso.…”

Section: Telomerization Of Isoprene With Aminesmentioning

confidence: 99%

Telomerization: Advances and Applications of a Versatile Reaction

et al. 2009

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“…The majority of these employ methanol as the nucleophile, [10,11] with a few examples using water [12,13] or amines. [14,15] To tackle the less reactive isoprene, we turned to Pd-carbene complexes, that were shown to be highly active and selective in several recent studies, [16][17][18][19] most notably by Beller and co-workers. [20][21][22] Since isoprene and glycerol are immiscible at practical concentrations, we achieved a monophasic reaction medium by adding various co-solvents.…”

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confidence: 99%

Palladium‐Catalysed Telomerisation of Isoprene with Glycerol and Polyethylene Glycol: A Facile Route to New Terpene Derivatives

Gordillo

Pachón²,

Jesús

et al. 2009

Adv Synth Catal

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We present here the first example of the telomerisation of isoprene with glycerol and polyethylene glycol (PEG-200), opening a facile route to new terpene structures, based on a combination of renewable and petroleum-based feedstocks. The reaction is catalysed by a palladium-carbene complex. Significantly, this system gives > 99% of linear monotelomer products. The factors that govern substrate conversion, dimerisation/telomerisation selectivity, and catalyst activity are studied and discussed.

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“…[12] Telomerization often occurs in the palladium-and nickel-catalyzed reactions. [13] Regioselectivity is also difficult to control, and mixtures of 1,2-and 1,4-addition products are often formed. In fact, mild and selective 1,2-hydroamination of dienes is rather rare, in particular, with a 1:1 ratio of nucleophile and diene employed to afford products in high yields.…”

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confidence: 99%