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Telomerization of Myrcene and Catalyst Separation by Thermomorphic Solvent Systems

Arno Behr, Leif Johnen, Andreas J. Vorholt

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Abstract

Abstract Telomerization of common petrochemical 1,3‐dienes such as butadiene and isoprene have long been successful with different nucleophiles; however, the telomerization of the C10 hydrocarbon myrcene was not known until now. Herein, the first telomerization of the monoterpene myrcene with diethylamine is discussed, which provides an atom‐economical way of generating C20 amines in a single step. Variation of the palladium precursors and phosphorous ligands and optimization of solvent and additives led to the optimum catalyst system [Pd(MeCN)4](BF4)2/PPh3. By using a thermomorphic solvent system, the Pd complex can be easily separated with low leaching values.

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What this paper is about

Abstract Telomerization of common petrochemical 1,3‐dienes such as butadiene and isoprene have long been successful with different nucleophiles; however, the telomerization of the C10 hydrocarbon myrcene was not known until now. Herein, the first telomerization of the monoterpene myrcene with diethylamine is discussed, which provides an atom‐economical way of generating C20 amines in a single step. Variation of the palladium precursors and phosphorous ligands and optimization of solvent and additives led to the optimum catalyst system [Pd(MeCN)4](BF4)2/PPh3. By using a thermomorphic solvent system, the Pd complex can be easily separated with low leaching values.

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Available abstract

Abstract Telomerization of common petrochemical 1,3‐dienes such as butadiene and isoprene have long been successful with different nucleophiles; however, the telomerization of the C10 hydrocarbon myrcene was not known until now. Herein, the first telomerization of the monoterpene myrcene with diethylamine is discussed, which provides an atom‐economical way of generating C20 amines in a single step. Variation of the palladium precursors and phosphorous ligands and optimization of solvent and additives led to the optimum catalyst system [Pd(MeCN)4](BF4)2/PPh3. By using a thermomorphic solvent system, the Pd complex can be easily separated with low leaching values.

Key concepts: Telomerization, Myrcene, Diethylamine, Chemistry, Palladium, Organic chemistry, Solvent, Nucleophile

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