Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

Xenia A. Barashkova; Mikhail J. Parulava; Yury N. Kotovshchikov; Gennadij V. Latyshev; Nikolay V. Lukashev; Irina P. Beletskaya

doi:10.1055/a-2236-8874

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(09): 1498-1504
DOI: 10.1055/a-2236-8874

paper

Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

Xenia A. Barashkova

,

Mikhail J. Parulava

,

Yury N. Kotovshchikov

,

Gennadij V. Latyshev∗

,

Nikolay V. Lukashev

,

Irina P. Beletskaya

Abstract

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Abstract

Alumina was found to activate Cu(I) catalysts in hydroboration of alkynes. This allowed to develop a simple and efficient protocol for hydroboration of alkynes with B₂Pin₂ using inexpensive CuCl/PPh₃ catalytic system. The approach does not require moisture-sensitive activators and stepwise preparation of ‘activated’ Cu complex. The developed conditions were applied to the preparation of β-styrylboronates from terminal and internal alkynes with excellent regio- and stereoselectivity. The procedure can also be extended to other terminal alkynes by the appropriate choice of ligand.

Key words

alumina - copper - hydroboration - alkynes - vinylboronic esters - stereoselective synthesis

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Referenzen

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