Work

Counterion Control oft‐BuO‐Mediated Single Electron Transfer to Nitrostilbenes to ConstructN‐Hydroxyindoles or Oxindoles

Year: 2021

Type: article

Abstract: tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202104319

Authors: Yingwei Zhao, Haoran Zhu, Siyoung Sung, Donald J. Wink, Joseph M. Zadrozny, Tom G. Driver

Institutions: Huaqiao University, University of Illinois Chicago, Colorado State University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: SusChEM: The Versatility of Electrophilic Metal N-Aryl Catalytic Intermediates for Carbon-Nitrogen Bond Formation, G6246951833, G9000347460