Lewis base promoted photoredox catalyzed addition of allylic radicals to Michael acceptors. (31st August 2022)

• Record Type: Journal Article
• Authors: Yan, Lu; Ulkoski, David; Puri, Taranee
• Is Part Of: Tetrahedron letters. Volume 105(2022)
• Publication Date: 2022-08-31
• Subjects: Photoredox -- Allylic boronic esters -- Ionizable lipids; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154057
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Upon activation via photoredox reaction conditions, allylic boronic esters can generate allylic radicals that react readily with Michael acceptors. The functionalized alkene products formed via this reaction can then be further transformed to other synthetically useful structures. As an example of this, we synthesized lipid-like structures that could be utilized for nucleic acid delivery. The robustness of these organoboronic reactions will allow for derivatization of these branched lipid structures where amino groups and aliphatic tails may be tuned to optimize these ionizable excipients.