Visible-Light-Catalyzed C–C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3‑Sulfonyl-1,2-dihydronaphthalenes
A novel visible-light-catalyzed sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of CC bond sulfonylation, C–C σ-bond cleavage, and intramolecular cycliz...
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Veröffentlicht in: | Journal of organic chemistry 2019-03, Vol.84 (5), p.2829-2839 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A novel visible-light-catalyzed sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of CC bond sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b03261 |