Copper‐Catalyzed Three‐Component Borylstannylation of Alkynes |
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Authors: | Yuki Takemoto Prof. Dr. Hiroto Yoshida Prof. Dr. Ken Takaki |
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Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi‐Hiroshima 739‐8527 (Japan), Fax: (+81)?82‐424‐5494 |
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Abstract: | Regio‐ and stereoselective installation of boryl and stannyl moieties into a carbon–carbon triple bond of various alkynes has been achieved based on a three‐component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate–tricyclohexylphosphine complex, giving diverse vic‐borylstannylalkenes in a straightforward manner. Carbon–tin and carbon–boron bonds of the resulting borylstannylation product are successively transformed into carbon–carbon bonds by a Migita–Kosugi–Stille and a Suzuki–Miyaura coupling, leading to the formation of (Z)‐tamoxifen with anti‐breast cancer activity. |
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Keywords: | alkynes boron copper tin total synthesis |
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