Year: 2026
Type: article
Abstract: N -Aryl hemiaminals are versatile synthetic intermediates that can serve as placeholders for N -aryliminium ions. We report the non-Kolbe electrolysis of N -arylamino acids using convenient, air-tolerant conditions with simple workup, user-friendly controls, and inexpensive electrode materials. We demonstrate the utility of these intermediates in traditional Povarov cyclizations (up to 70% yield over two steps) and the direct electrochemical synthesis of bioactive frameworks relevant to several natural products from simple N -arylamino acid starting materials.
Source: The Journal of Organic Chemistry
Institution: University of Delaware
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Discovery of Chemical Probes and Therapeutic Leads, Phase II, G335888736, G4040836280, CRIF:MU Cryprobe Upgrade of a NMR Spectrometer, Umpolung Methods with Electron Rich Aromatic Systems: Amine-Derived Reactive Intermediates in Synthesis, G501384772, G545157245, G5679962385, Acquisition of a 400 MHz NMR Spectrometer, Umpolung Methods with Electron Rich Aromatic Systems: Aza-ortho-Xylylenes, and N,N-Dialkylaniline N-Oxides in Synthesis, G6021491711, G737549599, High Performance Digital NMR Spectrometer, Acquisition of a Single-Crystal X-ray Diffractometer, G8414554082, Molecular Design of Advanced Biomaterials, High Sensitivity NMR Spectrometer with Cryoprobe, MRI: Acquisition of a High Resolution Mass Spectrometer for Small Molecule Analysis, Center for Biomedical Research Excellence in Multiscale Biomolecular Sensing (MBS), Q-Exactive Orbitrap LC-MC/MS System
OpenAlex ID: W7160551121