Overview
ABSTRACT
Because of global warming and in particular the excess carbon dioxide produced by human activities, it is becoming urgent to find alternatives to the use of fossil resources for organic synthesis. This article deals with the use of biomass-based hydrocarbons, namely terpenes, as a renewable carbon source. It discusses the development of a C-H activation reaction, and more specifically, a cross-dehydrogenative coupling between a terpene and an electron-poor alkene using palladium catalysis. A mechanistic study and an application of this transformation in micellar catalysis are then unveiled.
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Marco DI MATTEO: Doctorate from Sorbonne University - Paris Institute of Molecular Chemistry (IPCM, UMR 8232), CNRS - Sorbonne University, Paris, France - Institute of Chemical Research of Catalonia (ICIQ) - Barcelona Institute of Science and Technology (BIST), Tarragona, Spain
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Giovanni POLI: University Professor - Paris Institute of Molecular Chemistry (IPCM, UMR 8232), CNRS - Sorbonne University, Paris, France - Research Institute for Medicines (iMed ULisboa), Faculty of Pharmacy - Universidade de Lisboa, Lisbon, Portugal
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Alexandre PRADAL: CNRS Research Associate - Paris Institute of Molecular Chemistry (IPCM, UMR 8232), CNRS - Sorbonne University, Paris, France
INTRODUCTION
To respond to certain climate change-related issues in the synthesis of compounds of interest, new transformations and access to new synthons from biomass (a renewable carbon source) need to be developed. In most cases, organic compounds derived from biomass are functionalized (oxidized) molecules, unlike fossil fuels, which are composed solely of carbon and hydrogen atoms. However, there is a class of biobased compounds belonging to the hydrocarbon family. These molecules, known as terpenes, are found in the plant kingdom (plants, fruits, etc.) and are mainly known for their olfactory properties. However, they are rarely used as renewable resources in synthesis. One terpene in particular caught our attention because of its abundance and low cost: dextrorotatory limonene or (+)-limonene. This monoterpene, found mainly in citrus peel, was used as a molecular building block for the development of a dehydrogenating cross-coupling reaction. This transformation, carried out in the presence of a palladium complex, involves activation of the C–H bond of the exocyclic limonene alkene to form a conjugated diene. This study is complemented by an investigation of the reaction mechanism and by a post-functionalization in which one of the products formed is engaged in another coupling reaction in micellar medium, using water as solvent.
Key points
Field: Biomass valorization, catalysis
Degree of technology diffusion: Emergence
Technologies involved: Organic synthesis, organometallic catalysis, C activation–H
Applications: Organic chemistry
Main French players :
Competence centers: IPCM
Manufacturers: Novartis Pharma (Switzerland)
Contact: [email protected]
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KEYWORDS
catalysis | terpenes | C–H activation | cross-dehydrogenative coupling
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