Facile Synthesis of α-Boryl-Substituted Allylboronate Esters Using Stable Bis[(pinacolato)boryl]methylzinc Reagents

Org Lett. 2020 Mar 20;22(6):2476-2480. doi: 10.1021/acs.orglett.0c00721. Epub 2020 Mar 9.

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.