Transalkylation via C-N Bond Cleavage of Amines Catalyzed by Super Organophotoreductant CBZ6

The super organoreductant CBZ6-catalyzed tandem transalkylation-cyclization using amines as traceless radical donors and stabilizer is reported. The later-stage breaking of an N-C bond enables the transalkylation with a secondary amine as the leaving moiety. A wide range of tertiary amines were used as alkyl radical donors for the C1-C8 alkyls. This traceless stabilizer also enabled the transalkylation with methyl radical, which is normally not possible because of the instability of methyl radical.

Automated summary

This study reports a tandem transalkylation-cyclization reaction catalyzed by the super organoreductant CBZ6, using amines as traceless radical donors and stabilizers. The breaking of an N-C bond in the later stage allows transalkylation with a secondary amine as the leaving group. Various tertiary amines were successfully employed as alkyl radical donors. Additionally, the use of this traceless stabilizer enables transalkylation with methyl radical, which is typically unstable and difficult to use.