Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

Abstract
Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions.

Beilstein J. Org. Chem. 2024, 20, 264–271. doi:10.3762/bjoc.20.27

Source: Beilstein Journal of Organic Chemistry - February 12, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: amidyl radical cyclic voltammetry electrosynthesis hydroamination proton coupled electron transfer Full Research Paper Source Type: research