Stereoselective Access to Tetra‐ and Tri‐Substituted Fluoro‐ and Chloro‐Borylalkenes via Boron‐Wittig Reaction
Seungcheol Han, Yeosan Lee, Yujin Jung, Seung Hwan Cho
Abstract
Abstract Reported herein is the efficient synthesis of tetra‐ and tri‐substituted ( Z )‐fluoro‐ and ( Z )‐chloro‐borylalkenes by the Boron–Wittig reaction of ketones and aldehydes with bench‐top stable halo‐diborylmethanes. The substrate scope is broad and the Boron–Wittig reaction proceeds from a diverse range of ketones and aldehydes including biologically relevant molecules with fluoro‐ or chloro‐diborylmethanes, providing tetra‐ and tri‐substituted ( Z )‐fluoro‐ and ( Z )‐chloro‐borylalkenes in good yields with high stereoselectivity. The utilities of the obtained ( Z )‐fluoro‐ and ( Z )‐chloro‐borylalkenes are highlighted by further modifications to afford fluoroalkene derivatives or all‐carbon substituted alkene.