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TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions

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Abstract

A novel, efficient and metal-free cascade sulfonylation/cyclization of 2-propynolphenols with commercially available sodium sulfinates was developed for the synthesis of 4-sulfonyl 2H-chromenes under mild conditions. The reaction occurred by the sodium sulfinates’ nucleophilic addition of the allylene carbocation intermediate followed by a 6-endo-trig pathway. Additionally, this approach avoids the use of an oxidant or a photo-radical inducer and the reaction can tolerate a wide variety of functional groups in good yields.

Graphical abstract: TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions

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Publication details

The article was received on 02 Jun 2019, accepted on 17 Jul 2019 and first published on 19 Jul 2019


Article type: Research Article
DOI: 10.1039/C9QO00712A
Org. Chem. Front., 2019, Advance Article

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    TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions

    T. Yang, P. Kou, F. Jin, X. Song, J. Bai, H. Ding, Q. Xiao and Y. Liang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00712A

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