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Copper(I) Hydroxyapatite Catalyzed Sonogashira Reaction of Alkynes with Styrenyl Bromides. Reaction of cis-Styrenyl Bromides Forming Unsymmetric Diynes

Debasree Saha, Tanmay Chatterjee, Manabendra Mukherjee and Brindaban C. Ranu*

*Department of organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India, Email:

D. Saha, T. Chatterjee, M. Mukherjee, B. C. Ranu, J. Org. Chem., 2012, 77, 9379-9383.

DOI: 10.1021/jo3015819 (free Supporting Information)


An efficient Sonogashira coupling of terminal alkynes and styrenyl bromides is catalyzed by hydroxyapatite-supported copper(I). Trans-styrenyl bromides produce trans-enyne products, whereas cis-styrenyl bromides lead to unsymmetric 1,3-diynes by the cross coupling of terminal alkyne and the alkyne generated from the cis-styrenyl bromide.

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Key Words

Enynes, Diynes

ID: J42-Y2012-3390