A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions.
enantioselectivity
hydrogen bonds
organocatalysis
photochemistry
sensitizers
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
21 Apr 2020
21 Apr 2020
Historique:
received:
10
02
2020
pubmed:
18
2
2020
medline:
18
2
2020
entrez:
18
2
2020
Statut:
ppublish
Résumé
A chiral phosphoric acid with a 2,2'-binaphthol core was prepared that displays two thioxanthone moieties at the 3,3'-position as light-harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of β-carboxyl-substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates.
Identifiants
pubmed: 32065432
doi: 10.1002/chem.202000720
pmc: PMC7216904
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5190-5194Subventions
Organisme : Verband der Chemischen Industrie
Organisme : Deutsche Forschungsgemeinschaft
ID : SPP 1807
Organisme : H2020 European Research Council
ID : 665951
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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