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

Org Lett. 2023 Oct 20;25(41):7518-7522. doi: 10.1021/acs.orglett.3c02827. Epub 2023 Oct 5.

Abstract

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.