Copper-catalyzed boroacylation of allenes to access tetrasubstituted vinylboronates
Bing-Xue Shen, Xiang‐Ting Min, Yan‐Cheng Hu, Lei-Lei Qian, Sa‐Na Yang, Boshun Wan, Qing‐An Chen
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.
Topics & Concepts
ChemistryCatalysisCopperCombinatorial chemistryOrganic chemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods