Palladium-catalyzed hydroamination of farnesene—Long chain amines as building blocks for surfactants based on a renewable feedstock

Faßbach, Thiemo A.; Gösser, Nadine; Sommer, Fridolin O.; Behr, Arno; Guo, Xiaoqiang; Romanski, Steffen; Leinweber, Dirk; Vorholt, Andreas J.

doi:10.1016/j.apcata.2017.06.014

Cited by 8 publications

(4 citation statements)

References 31 publications

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“…Another terpene that is a promising building block for valuable chemicals is β‐farnesene, which has recently become available on a larger scale. It is produced by yeast fermentation and has attracted attention in both academic and industrial research and development. Since the large and bulky substituent is located at the 2 nd position, the 1,3‐diene unit is prone to conversion with nucleophiles, even during telomerization with amines .…”

Section: 3‐dienesmentioning

confidence: 99%

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

2019

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Telomerization is a versatile tool for synthesizing unsaturated ethers, amines and other molecules starting from 1,3‐dienes and respective nucleophiles. The homogeneously catalyzed reaction has been the subject of academic and industrial research for over 50 years, offering a broad variety of substrates, catalysts and process concepts. This Minireview presents the advances and developments in this field over the last decade. The focus was on the conversion of renewable resources, the synthesis of promising new products and the development of efficient process concepts to combine these.

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Section: 3‐dienesmentioning

confidence: 99%

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

2019

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“…Our group developed a catalytic system for the hydroamination of β ‐farnesene with diethylamine as nucleophile and achieved excellent yields. As shown in Figure , hydroamination yields four different isomers depending on the site of the nucleophile's attack …”

Section: C6 Molecules (Renewables)mentioning

confidence: 82%

“…The reaction was successfully scaled up in our group to a 5 L batch. At 100 °C and a reaction time of 5 hours, yields of the respective diethylfarnesyl amines were greater than 90 % . As already discussed above for telomerization of butadiene and hydroamination of β ‐myrcen, hydroamination of β ‐farnesene is also feasible with DIMCARB.…”

Section: C6 Molecules (Renewables)mentioning

confidence: 99%

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

et al. 2018

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For many years, the efficient use of resources has been a major and permanent challenge for the chemical industry. The implementation of alternative resources such as renewables and carbon dioxide has been a subject of considerable discussion, but also the more efficient use of long known bulk chemicals is of great interest. Among them, 1,3‐dienes such as 1,3‐butadiene from the C4 cut of the naphtha cracker as well as isoprene, piperylene and cyclopentadiene from the corresponding C5 section are important substrates. These dienes are presently employed in various markets, with the greatest importance being in the production of polymers and copolymers. However, homogeneous transition metal catalysis has proven to be a versatile tool to functionalize these important 1,3‐dienes to low molecular weight fine chemicals by introducing, for example, nitrogen, oxygen or silicon. Hence, an upgraded use of the corresponding products as agrochemicals, pharmaceuticals, fragrances or special detergents is close at hand. The main approaches in the topic of homogeneous functionalization reactions of the industrially relevant 1,3‐dienes will be summarized and discussed within the present article. Besides that, novel applications including renewable 1,3‐dienes, for example β‐myrcene and β‐farnesene, as well as the application of CO2 in telomerization, will be critically discussed.

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“…In this context, very recently, we reported the palladium catalysed hydroamination of β ‐farnesene as an elegant method to obtain terpene derived surfactants with 100% atom economy ,…”

Section: Introductionmentioning

confidence: 99%

Terpene‐Derived Highly Branched C₃₀‐Amines via Palladium‐Catalysed Telomerisation of β‐Farnesene

et al. 2018

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The synthesis of highly branched long chain amines in one step is still a challenge. The palladium catalysed telomerisation of the renewable sesquiterpene b-farnesene with secondary amines yields such tertiary amines and thus, was investigated within this work. Preliminary, a suitable palladium catalyst system was developed by a high-throughput screening. It efficiently allows for the synthesis of tertiary amines with a highly branched C 30 -carbon chain with yields up to 94% of the corresponding desired allylic C 30 -amines. The generality of the protocol was proven for thirteen amines with linear and branched alkyl and aryl groups. A clear correlation between the scaffold of the amine, basicity and the activity as nucleophile in the telomerisation was uncovered. Based on the different polarities of the nonpolar in-situ formed C 30 -substituted tertiary amines and the polar solvent, a proof of concept for catalyst recovery by simple decantation was shown.

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Palladium-catalyzed hydroamination of farnesene—Long chain amines as building blocks for surfactants based on a renewable feedstock

Cited by 8 publications

References 31 publications

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

Terpene‐Derived Highly Branched C₃₀‐Amines via Palladium‐Catalysed Telomerisation of β‐Farnesene

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Palladium-catalyzed hydroamination of farnesene—Long chain amines as building blocks for surfactants based on a renewable feedstock

Cited by 8 publications

References 31 publications

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

Terpene‐Derived Highly Branched C30‐Amines via Palladium‐Catalysed Telomerisation of β‐Farnesene

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Terpene‐Derived Highly Branched C₃₀‐Amines via Palladium‐Catalysed Telomerisation of β‐Farnesene