Modifying Woodward-Hoffmann Stereoselectivity Under Vibrational Strong Coupling.
Woodward-Hoffmann rules
electrocyclic ring opening
orbital symmetry
pericyclic reactions
strong coupling
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 Mar 2021
08 Mar 2021
Historique:
received:
06
10
2020
revised:
18
11
2020
pubmed:
12
12
2020
medline:
12
12
2020
entrez:
11
12
2020
Statut:
ppublish
Résumé
Vibrational strong coupling (VSC) has recently been shown to change the rate and chemoselectivity of ground-state chemical reactions via the formation of light-matter hybrid polaritonic states. However, the observation that vibrational-mode symmetry has a large influence on charge-transfer reactions under VSC suggests that symmetry considerations could be used to control other types of chemical selectivity through VSC. Here, we show that VSC influences the stereoselectivity of the thermal electrocyclic ring opening of a cyclobutene derivative, a reaction which follows the Woodward-Hoffmann rules. The direction of the change in stereoselectivity depends on the vibrational mode that is coupled, as do changes in rate and reaction thermodynamics. These results on pericyclic reactions confirm that symmetry plays a key role in chemistry under VSC.
Identifiants
pubmed: 33305864
doi: 10.1002/anie.202013465
pmc: PMC7986062
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5712-5717Subventions
Organisme : Agence Nationale de la Recherche
ID : ANR-18-QUAN-0005-01
Organisme : Agence Nationale de la Recherche
ID : ANR-10-EQPX-52-01
Organisme : Agence Nationale de la Recherche
ID : ANR-10-LABX- 0026 CSC
Organisme : H2020 European Research Council
ID : 788482
Organisme : H2020 European Research Council
ID : 639170
Organisme : H2020 Marie Skłodowska-Curie Actions
ID : 792101
Informations de copyright
© 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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