The Interplay between Kinetics and Thermodynamics in Furan Diels–Alder Chemistry for Sustainable Chemicals Production

Biomass‐derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels–Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom‐efficient ways. Despite nearly...

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Veröffentlicht in:Angewandte Chemie International Edition Jg. 61; H. 17; S. e202114720 - n/a
Hauptverfasser: Cioc, Răzvan C., Crockatt, Marc, Waal, Jan C., Bruijnincx, Pieter C. A.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Germany Wiley Subscription Services, Inc 19.04.2022
John Wiley and Sons Inc
Ausgabe:International ed. in English
Schlagworte:
Alkenes
Chemicals
Chemistry
Cycloaddition
Cycloaddition Reaction
Diels-Alder reactions
Diels–Alder reaction
Functional materials
furan
Furans
Furans - chemistry
green chemistry
Kinetics
Pesticides
Renewable resources
Review
Reviews
Sustainable production
Sustainable yield
Thermodynamics
thermodynamics
Diels-Alder reaction
furan
kinetics
green chemistry
ISSN:1433-7851, 1521-3773, 1521-3773
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Abstract Biomass‐derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels–Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom‐efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure–reactivity–stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron‐rich furans and electron‐deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production. The furan Diels–Alder (DA) cycloaddition is a powerful green methodology to upgrade bio‐derived resources into valuable, renewable chemical products. The intricate interplay between kinetics and thermodynamics often complicates the understanding of this chemistry. In this review we provide simple structure–reactivity–stability relationships to guide future efforts in the design of efficient new synthesis routes based on furan DA reactions.
AbstractList Biomass-derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels-Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom-efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure-reactivity-stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron-rich furans and electron-deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production.Biomass-derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels-Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom-efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure-reactivity-stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron-rich furans and electron-deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production.
Biomass‐derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels–Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom‐efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure–reactivity–stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron‐rich furans and electron‐deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production. The furan Diels–Alder (DA) cycloaddition is a powerful green methodology to upgrade bio‐derived resources into valuable, renewable chemical products. The intricate interplay between kinetics and thermodynamics often complicates the understanding of this chemistry. In this review we provide simple structure–reactivity–stability relationships to guide future efforts in the design of efficient new synthesis routes based on furan DA reactions.
Biomass‐derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels–Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom‐efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure–reactivity–stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron‐rich furans and electron‐deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production. The furan Diels–Alder (DA) cycloaddition is a powerful green methodology to upgrade bio‐derived resources into valuable, renewable chemical products. The intricate interplay between kinetics and thermodynamics often complicates the understanding of this chemistry. In this review we provide simple structure–reactivity–stability relationships to guide future efforts in the design of efficient new synthesis routes based on furan DA reactions.
Biomass-derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels-Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom-efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure-reactivity-stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron-rich furans and electron-deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production.
Author Waal, Jan C.
Bruijnincx, Pieter C. A.
Crockatt, Marc
Cioc, Răzvan C.
AuthorAffiliation 1 Organic Chemistry and Catalysis Debye Institute for Nanomaterials Science Faculty of Science Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands
2 Department of Sustainable Process and Energy Systems, TNO Leeghwaterstraat 44 2628 CA Delft The Netherlands
AuthorAffiliation_xml – name: 2 Department of Sustainable Process and Energy Systems, TNO Leeghwaterstraat 44 2628 CA Delft The Netherlands
– name: 1 Organic Chemistry and Catalysis Debye Institute for Nanomaterials Science Faculty of Science Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands
Author_xml – sequence: 1
  givenname: Răzvan C.
  surname: Cioc
  fullname: Cioc, Răzvan C.
  organization: Utrecht University
– sequence: 2
  givenname: Marc
  surname: Crockatt
  fullname: Crockatt, Marc
  organization: Department of Sustainable Process and Energy Systems, TNO
– sequence: 3
  givenname: Jan C.
  orcidid: 0000-0002-9830-6109
  surname: Waal
  fullname: Waal, Jan C.
  organization: Department of Sustainable Process and Energy Systems, TNO
– sequence: 4
  givenname: Pieter C. A.
  orcidid: 0000-0001-8134-0530
  surname: Bruijnincx
  fullname: Bruijnincx, Pieter C. A.
  email: p.c.a.bruijnincx@uu.nl
  organization: Utrecht University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/35014138$$D View this record in MEDLINE/PubMed
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Issue 17
Keywords thermodynamics
Diels-Alder reaction
furan
kinetics
green chemistry
Language English
License Attribution-NonCommercial
2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
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Snippet Biomass‐derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the...
Biomass-derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the...
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SubjectTerms Alkenes
Chemicals
Chemistry
Cycloaddition
Cycloaddition Reaction
Diels-Alder reactions
Diels–Alder reaction
Functional materials
furan
Furans
Furans - chemistry
green chemistry
Kinetics
Pesticides
Renewable resources
Review
Reviews
Sustainable production
Sustainable yield
Thermodynamics
Title The Interplay between Kinetics and Thermodynamics in Furan Diels–Alder Chemistry for Sustainable Chemicals Production
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202114720
https://www.ncbi.nlm.nih.gov/pubmed/35014138
https://www.proquest.com/docview/2649290192
https://www.proquest.com/docview/2618905307
https://pubmed.ncbi.nlm.nih.gov/PMC9304315
Volume 61
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