Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

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

Publication History

Received: 15 November 2023

Accepted after revision: 02 January 2024

Accepted Manuscript online:
02 January 2024

Article published online:
31 January 2024

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