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Issue 11, 2017
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The photochemical alkylation and reduction of heteroarenes

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Abstract

The functionalization of heteroarenes has been integral to the structural diversification of medicinally active molecules such as quinolines, pyridines, and phenanthridines. Electron-deficient heteroarenes are electronically compatible to react with relatively nucleophilic free radicals such as hydroxyalkyl. However, the radical functionalization of such heteroarenes has been marked by the use of transition-metal catalyzed processes that require initiators and stoichiometric oxidants. Herein, we describe the photochemical alkylation of quinolines, pyridines and phenanthridines, where through direct excitation of the protonated heterocycle, alcohols and ethers, such as methanol and THF, can serve as alkylating agents. We also report the discovery of a photochemical reduction of these heteroarenes using only iPrOH and HCl. Mechanistic studies to elucidate the underlying mechanism of these transformations, and preliminary results on catalytic methylations are also reported.

Graphical abstract: The photochemical alkylation and reduction of heteroarenes

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Supplementary files

Article information


Submitted
28 Aug 2017
Accepted
09 Sep 2017
First published
11 Sep 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 7412-7418
Article type
Edge Article

The photochemical alkylation and reduction of heteroarenes

T. McCallum, S. P. Pitre, M. Morin, J. C. Scaiano and L. Barriault, Chem. Sci., 2017, 8, 7412
DOI: 10.1039/C7SC03768F

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