Visible‐Light‐Promoted Reaction of N‐Hydroxyphthalimide Esters with Vinyl Boronic Pinacol Ester

• Published in: European journal of organic chemistry Vol. 26; no. 15
• Main Authors: Gkizis, Petros L., Triandafillidi, Ierasia, Stini, Naya A., Batsika, Charikleia S., Kokotos, Christoforos G.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 14-04-2023
• Subjects: amino acids; boron; Esters; Giese reaction; photochemistry; radical addition; Substrates
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202300152

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.
A light‐driven protocol to access alkyl boronic acid pinacol esters from vinyl boronate using N‐hydroxyphthalimide esters as the alkyl generator was developed. A good substrate scope was examined, demonstrating good to high yields and excellent functional group tolerance.