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Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules

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Organometallics and Renewables

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 39))

Abstract

The dimerization of 1,3-dienes (e.g. butadiene) with the addition of a protic nucleophile (e.g. methanol) yields 2,7-octadienyl ethers in the so-called telomerization reaction. This reaction is most efficiently catalyzed by homogeneous palladium complexes. The field has experienced a renaissance in recent years as many of the platform molecules that can be renewably obtained from biomass are well-suited to act as multifunctional nucleophiles in this reaction. In addition, the process adheres to many of the principles of green chemistry, given that the reaction is 100% atom efficient and produces little waste. The telomerization reaction thus provides a versatile route for the production of valuable bulk and specialty chemicals that are (at least partly) green and renewable. The use of various multifunctional substrates that can be obtained from biomass is covered in this review, as well as mechanistic aspects of the telomerization reaction.

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Acknowledgements

PCAB and BMW gratefully thank the Smart Mix programme of the Netherlands Ministry of Economic Affairs and the Netherlands Ministry of Education, Culture and Science within the framework of the CatchBio programme. The authors also kindly thank the ACTS-ASPECT programme for financial support. PCAB also gratefully acknowledges NWO for a Veni grant.

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Authors and Affiliations

  1. Inorganic Chemistry and Catalysis Group, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands

    Pieter C. A. Bruijnincx, Robin Jastrzebski, Peter J. C. Hausoul & Bert M. Weckhuysen

  2. Organic Chemistry and Catalysis Group, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands

    Peter J. C. Hausoul & Robertus J. M. Klein Gebbink

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  1. Pieter C. A. Bruijnincx
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  2. Robin Jastrzebski
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  5. Bert M. Weckhuysen
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Correspondence to Pieter C. A. Bruijnincx or Bert M. Weckhuysen .

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  1. , Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, Karlsruhe, 76131, Germany

    Michael A.R. Meier

  2. , Debye Institute of Nanomaterials Science, Utrecht University, Universiteitsweg 99, Utrecht, 3584, Netherlands

    Bert M. Weckhuysen

  3. , Debye Institute of Nanomaterials Science, Utrecht University, Universiteitsweg 99, Utrecht, 3584, Netherlands

    Pieter C. A. Bruijnincx

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Bruijnincx, P.C.A., Jastrzebski, R., Hausoul, P.J.C., Gebbink, R.J.M.K., Weckhuysen, B.M. (2012). Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules. In: Meier, M., Weckhuysen, B., Bruijnincx, P. (eds) Organometallics and Renewables. Topics in Organometallic Chemistry, vol 39. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-28288-1_2

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