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 Jg. 134; H. 17
Hauptverfasser: Cioc, Răzvan C., Crockatt, Marc, Waal, Jan C., Bruijnincx, Pieter C. A.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Weinheim Wiley Subscription Services, Inc 19.04.2022
Schlagworte:
Alkenes
Chemicals
Chemistry
Cycloaddition
Diels-Alder reactions
Diels–Alder reaction
Functional materials
furan
Furans
green chemistry
Kinetics
Pesticides
Renewable resources
Sustainable production
Sustainable yield
Thermodynamics
ISSN:0044-8249, 1521-3757
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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. 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.
Author Waal, Jan C.
Bruijnincx, Pieter C. A.
Crockatt, Marc
Cioc, Răzvan C.
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
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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...
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SubjectTerms Alkenes
Chemicals
Chemistry
Cycloaddition
Diels-Alder reactions
Diels–Alder reaction
Functional materials
furan
Furans
green chemistry
Kinetics
Pesticides
Renewable resources
Sustainable production
Sustainable yield
Thermodynamics
Title The Interplay between Kinetics and Thermodynamics in Furan Diels–Alder Chemistry for Sustainable Chemicals Production
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