Visible‐Light‐Promoted Reaction of <i>N</i>‐Hydroxyphthalimide Esters with Vinyl Boronic Pinacol Ester
Petros L. Gkizis, Ierasia Triandafillidi, Naya A. Stini, Charikleia S. Batsika, Christoforos G. Kokotos
Abstract
Abstract A novel and easy‐to‐execute light‐driven protocol for the preparation of alkyl boronic acid pinacol esters from vinyl boronate using N ‐hydroxyphthalimide esters as the potential precursor is described. In this photochemical protocol, the N ‐hydroxyphthalimide ester's fragmentation generates C‐centered radicals, which undergo a radical Michael addition to vinyl boronic pinacol ester furnishing the desired products. A good substrate scope having various functionalities is presented and good to high yields are obtained.
Topics & Concepts
PinacolChemistryBoronic acidRadicalAlkylOrganic chemistrySubstrate (aquarium)Combinatorial chemistryCatalysisGeologyOceanographyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods