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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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Publication details

The article was received on 28 Aug 2017, accepted on 09 Sep 2017 and first published on 11 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC03768F
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    The photochemical alkylation and reduction of heteroarenes

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

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