C(sp2)-Arylsulfones Directly from Arylsulfonyl Chlorides with Boronic Acids by Photoactivation of Boosted EDA Complexes.
EDA complexes
boronic acids
photoredox
sulfones
sulfonyl chlorides
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 Oct 2024
21 Oct 2024
Historique:
revised:
13
10
2024
received:
18
09
2024
accepted:
21
10
2024
medline:
22
10
2024
pubmed:
22
10
2024
entrez:
22
10
2024
Statut:
aheadofprint
Résumé
Directly with arylsulfonyl chlorides, a green and efficient deborylativesulfonylation of aryl(alkenyl)boronic acids has been developed to access both diarylsulfones and vinylarylsulfones in moderate to excellent yields at room temperature under visible-light irradiation. This protocol features broad C(sp2)-arylsulfone applicability, simple operation, accessibility of raw materials and ease of scale-up. The key to the success of this photoredox transformation is introducing catalytic amounts of additives, naphthalen-2-ols, thus boosting the formed electron donor-acceptor (EDA) complexes, which can dramatically improve not only the reaction efficiency but also the selectivity. This strategy was inspired and derived from specific substrates, representing a rare paradigm of how to exploit a more general reaction system. Moreover, extensive control experiments provide insights into the proposed mechanism.
Identifiants
pubmed: 39434238
doi: 10.1002/chem.202403487
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202403487Informations de copyright
© 2024 Wiley‐VCH GmbH.