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Cross Coupling of Bis[(E)-2-bromovinyl)] Selenide with Terminal Acetylenes in the Presence of Pd(PPh3)4: the First Example of the Sonogashira Cross Coupling Involving Vinyl Selenide

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Abstract

Bis[(E)-2-bromovinyl] selenide enters cross coupling with terminal acetylenes in the presence of a Pd/CuI catalyst at room temperature. The reaction involves both the bromine atom and the selanyl function and leads to both substituted bis(but-1-en-3-ynyl) selenides and enediynes with complete retention of the configuration of the parent selenide.

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ACKNOWLEDGMENTS

The authors are grateful to the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences, for spectral and analytical studies.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    A. V. Martynov, N. A. Makhaeva, M. V. Musalov & S. V. Amosova

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  1. A. V. Martynov
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  2. N. A. Makhaeva
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  3. M. V. Musalov
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  4. S. V. Amosova
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Correspondence to A. V. Martynov.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 11, pp. 1641–1646 https://doi.org/10.31857/S0514749221110100.

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Martynov, A.V., Makhaeva, N.A., Musalov, M.V. et al. Cross Coupling of Bis[(E)-2-bromovinyl)] Selenide with Terminal Acetylenes in the Presence of Pd(PPh3)4: the First Example of the Sonogashira Cross Coupling Involving Vinyl Selenide. Russ J Org Chem 57, 1882–1886 (2021). https://doi.org/10.1134/S1070428021110117

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