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DOI: 10.1055/s-0037-1611527
Intermolecular Reactions of Pyridyl Radicals with Olefins via Photoredox Catalysis
Financial support for this work was provided by startup funds from Emory University and the National Institutes of Health (GM129495).Publication History
Received: 01 March 2019
Accepted after revision: 04 April 2019
Publication Date:
24 April 2019 (online)
Abstract
Pyridines are valuable motifs in a number of bioactive and functional molecules. The chemoselective functionalization of these structures from stable and widely available starting materials is a meaningful goal. We have demonstrated selective formation of pyridyl radicals at any position (2-, 3-, 4-pyridyl), through the action of a reducing photoredox catalyst. These radicals readily engage alkenes to deliver high-value products. Alteration of the reaction medium has enabled the use of a diverse range of alkene subtypes in a highly divergent and chemoselective manner.
1 Introduction
2 Minisci-Type Pyridine Alkylation
3 An Alternate Approach – Reductive Radical Formation
4 Conjugate Addition of Pyridyl Radicals
5 Radical Hydroarylation of Neutral and Rich Olefins
6 Solvent-Based Chemoselectivity
7 Summary and Outlook
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