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
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

e202403487

Informations de copyright

© 2024 Wiley‐VCH GmbH.

Auteurs

Nianting Yuan (N)

Wuhan University of Technology, Chemistry, CHINA.

Sen Chen (S)

Wuhan University of Technology, Chemistry, CHINA.

Yuanxin Liu (Y)

Wuhan University of Technology, Chemistry, CHINA.

Min Chen (M)

Wuhan University of Technology, chemistry, Luoshi Road 205, 430070, Wuhan, CHINA.

Classifications MeSH