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Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction.

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A copper-catalyzed three-component reaction of terminal alkynes, diazo compounds, and B2pin2 to prepare trisubstituted alkenylboronates has been developed. This difunctionalization of alkynes selectively occurs at the terminal carbon atom and… Click to show full abstract

A copper-catalyzed three-component reaction of terminal alkynes, diazo compounds, and B2pin2 to prepare trisubstituted alkenylboronates has been developed. This difunctionalization of alkynes selectively occurs at the terminal carbon atom and proceeds via a tandem sequence. The copper catalyst plays dual roles in the whole process, namely, the initial copper-catalyzed cross-coupling and the following copper-catalyzed stereoselective boration reaction. Typically, different carbene precursors selectively lead to Z- and E-alkenes.

Keywords: copper; terminal alkynes; three component; component reaction; copper catalyzed

Journal Title: Organic letters
Year Published: 2021

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