Synlett 2019; 30(14): 1607-1614
DOI: 10.1055/s-0037-1611527
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© Georg Thieme Verlag Stuttgart · New York

Intermolecular Reactions of Pyridyl Radicals with Olefins via Photoredox Catalysis

Ciaran P. Seath
,
Nathan T. Jui*
Department of Chemistry, Winship Cancer Institute, Emory University, Atlanta, GA 30322, USA   eMail: njui@emory.edu
› Institutsangaben
Financial support for this work was provided by startup funds from Emory University and the National Institutes of Health (GM129495).
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Publikationsverlauf

Received: 01. März 2019

Accepted after revision: 04. April 2019

Publikationsdatum:
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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