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Silver-mediated oxidative C–C bond sulfonylation/arylation of methylenecyclopropanes with sodium sulfinates: facile access to 3-sulfonyl-1,2-dihydronaphthalenes

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Abstract

The novel AgNO3-mediated oxidative sulfonylation/arylation of a C–C σ-bond in methylenecyclopropanes with sodium sulfinates to synthesize various 3-sulfonylated 1,2-dihydronaphthalenes is reported. This sulfonylation/arylation transformation proceeds via a sequence of sulfonylation, C–C σ-bond cleavage and intramolecular cyclization, and the experimental results show that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for the difunctionalization of C–C bonds with a phenyl ring and a sulfonyl radical via the one-pot construction of a C–S bond and a new C–C bond.

Graphical abstract: Silver-mediated oxidative C–C bond sulfonylation/arylation of methylenecyclopropanes with sodium sulfinates: facile access to 3-sulfonyl-1,2-dihydronaphthalenes

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Publication details

The article was received on 06 Dec 2018, accepted on 26 Dec 2018 and first published on 27 Dec 2018


Article type: Communication
DOI: 10.1039/C8OB03045F
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Silver-mediated oxidative C–C bond sulfonylation/arylation of methylenecyclopropanes with sodium sulfinates: facile access to 3-sulfonyl-1,2-dihydronaphthalenes

    Y. Liu, Q. Wang, Z. Chen, Q. Zhou, C. Zhou, B. Xiong, P. Zhang, C. Yang and K. Tang, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB03045F

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