Nickel-Catalyzed Sulfonylation of Aryl Bromides Enabled by Potassium Metabisulfite as a Uniquely Effective SO
Mechanism
Nickel
Reductive Coupling
Sulfonylation
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:
02 May 2023
02 May 2023
Historique:
received:
29
11
2022
medline:
11
3
2023
pubmed:
11
3
2023
entrez:
10
3
2023
Statut:
ppublish
Résumé
The development and mechanistic investigation of a nickel-catalyzed sulfonylation of aryl bromides is disclosed. The reaction proceeds in good yields for a variety of substrates and utilizes an inexpensive, stench-free, inorganic sulfur salt (K
Identifiants
pubmed: 36897277
doi: 10.1002/anie.202217623
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202217623Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
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K2S2O5 cost=$43.46/mol SO2 equiv, Sigma-Aldrich 01/24/2022.
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We have since continued development toward a manufacturing process utilizing TMP as a non-toxic methylating reagent. These parameters are not feasible on smaller scales and it was decided that methyliodide, despite its toxicity, was suitable on smaller scales. The development of this process will be reported in due course.
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In cases of low yielding substrates, the bromides either failed or were sluggish to react to form the sulfinate. Competing hydrodehalogenation of the aryl bromide can also be a substrate specific issue. The hydrodehalogention was solved separately during process optimization, which will be reported in due course. See Supporting Information for additional problematic substrates.