Diboron reagents in the deoxygenation of nitrones. Issue 4 (4th January 2023)

• Record Type: Journal Article
• Authors: Vargas, Emily L.; Franco, Mario; Alonso, Inés; Tortosa, Mariola; Belén Cid, M.
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 4(2023)
• Page Start: 807
• Page End: 816
• Publication Date: 2023-01-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01880b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : B2 nep2 efficiently cleaves the N–O bond of nitrones through a concerted mechanism to form imines in very high yields via a simple, efficient and scalable protocol. Typical radical traps like DMPO and TEMPO are also deoxygenated by diboron reagents. Abstract : B2 nep2 efficiently promotes the N–O cleavage of nitrones to form imines in very high yields via a simple, efficient, sustainable, functional group tolerant and scalable protocol. The reaction occurs in the absence of additives through a concerted mechanism. We demonstrated that DMPO and TEMPO, typically used as radical traps, are also deoxygenated by diboron reagents, which demonstrates their limitation as mechanistic probes.