Diboron reagents in the deoxygenation of nitrones

B(2)nep(2) 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.

Automated summary

B(2)nep efficiently promotes N-O cleavage of nitrones to form imines in 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 showed that DMPO and TEMPO, typically used as radical traps, are also deoxygenated by diboron reagents, revealing their limitations as mechanistic probes.