Facile Synthesis of α-Boryl-Substituted Allylboronate Esters Using Stable Bis[(pinacolato)boryl]methylzinc Reagents
Minkyeong Shin, Minjae Kim, Chiwon Hwang, Hyojae Lee, Hyunchul Kwon, Jinyoung Park, Eunsung Lee, Seung Hwan Cho
Abstract
Reported herein is the utilization of bis[(pinacolato)boryl]methylzinc halides, whose structures are characterized via single-crystal X-ray analysis, as solid storable reagents for copper-catalyzed coupling with vinyliodonum salts. The reaction proceeds under mild conditions and shows broad scope with respect to vinyliodonium salts, affording various α-boryl-substituted allylboronate esters in good yields. Synthetic applications of the obtained products are also demonstrated.
Topics & Concepts
ChemistryReagentHalideCombinatorial chemistryReaction conditionsCatalysisBoronOrganic chemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods