Electrochemical hydrogen isotope exchange of amines controlled by alternating current frequency.

ABSTRACT: Here, we report an electrochemical protocol for hydrogen isotope exchange (HIE) at α-C(sp³)-H amine sites. Tetrahydroisoquinoline and pyrrolidine are selected as two model substrates because of their different proton transfer (PT) and hydrogen atom transfer (HAT) kinetics at the α-C(sp³)-H amine sites, which are utilized to control the HIE reaction outcome at different applied alternating current (AC) frequencies. We found the highest deuterium incorporation for tetrahydroisoquinolines at 0 Hz (i.e., under direct current (DC) electrolysis conditions) and pyrrolidines at 0.5 Hz. Analysis of the product distribution and D isotope incorporation at different frequencies reveals that the HIE of tetrahydroisoquinolines is limited by its slow HAT, whereas the HIE of p

SUBMITTER: Behera N 

PROVIDER: S-EPMC10796833 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature