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 CC 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
Hauptverfasser: Liu, Yu, Wang, Qiao-Lin, Chen, Zan, Zhou, Quan, Li, Hua, Zhou, Cong-Shan, Xiong, Bi-Quan, Zhang, Pan-Liang, Tang, Ke-Wen
Format: Artikel
Sprache:eng
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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 CC 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03261