Copper-catalyzed boroacylation of allenes to access tetrasubstituted vinylboronates†
Abstract
A distinct copper-catalyzed boroacylation of allenes with acyl chlorides and bis(pinacolato)diboron is developed. For aromatic acyl chlorides, 1,2-boroacylation of allenes readily takes place, leading to the formation of tetrasubstituted vinylboronates with exclusive (E)-stereoselectivity. In comparison, the employment of alkyl acyl chlorides as electrophiles alters the selectivity to 2,3-boroacylated products. Additionally, the product can easily undergo Suzuki–Miyaura cross-coupling to afford tetrasubstituted alkene with complete retention of the configuration.
- This article is part of the themed collection: Synthetic methodology in OBC
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