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Plant coumarins: XI. Cross coupling reactions with 2-(tosyl)oreoselone

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Abstract

The reaction of a linearly fused furocoumarin, oreoselone, with p-toluenesulfonyl chloride gave 2-tosyloreoselone which showed a high reactivity in palladium-catalyzed cross-coupling reactions with formation of a new carbon-carbon bond. 2-Tosyloreoselone reacted with terminal alkynes in the presence of Pd(PPh3)2Cl2 to give the corresponding 2-alkynylfuro[3,2-g]chromen-3-ones. 2-Aryl(hetaryl)alkynyloreoselones were obtained in high yield directly by palladium-catalyzed reaction of oreoselone with tosyl chloride and aryl(hetaryl)acetylenes. The reaction of 2-tosyloreoselone with aryl(hetaryl)boronic acids in the presence of palladium complexes with uni- and bidentate ligands, tetrabutylammonium bromide, and a base afforded 2-aryl(hetaryl)-substituted oreoselones. 2-Vinyloreoselone was synthesized from 2-tosyloreoselone and potassium trifluoro(vinyl)borate.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    A. B. Lipeeva, E. E. Shul’ts, M. M. Shakirov & G. A. Tolstikov

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  1. A. B. Lipeeva
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  2. E. E. Shul’ts
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  3. M. M. Shakirov
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  4. G. A. Tolstikov
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Correspondence to E. E. Shul’ts.

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Original Russian Text © A.B. Lipeeva, E.E. Shul’ts, M.M. Shakirov, G.A. Tolstikov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 1, pp. 105–112.

For communication X, see [1].

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Lipeeva, A.B., Shul’ts, E.E., Shakirov, M.M. et al. Plant coumarins: XI. Cross coupling reactions with 2-(tosyl)oreoselone. Russ J Org Chem 49, 99–107 (2013). https://doi.org/10.1134/S107042801301017X

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  • DOI: https://doi.org/10.1134/S107042801301017X

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