Alkoxides have been utilized to unlock new reactivities on nitroarenes. Exposure of nitrostibenes to tert-butoxide was found to afford N-hydroxyindoles when the counterion is sodium, and yield oxindoles because of the change of alkoxide to potassium tert-butoxide, going through a novel dioxygen-transfer process followed by a 1,2-phenyl migration. Mechanistic studies showed that radical intermediates were generated during the reaction process and a counterion coordination control was inferred to influence whether an oxindole or N-hydroxyindole product is formed.

Counterion control of t-BuO-mediated single electron transfer to nitrostilbenes constructs N-hydroxyindoles or oxindoles

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.