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Issue 3, 2016
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Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction

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Abstract

A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to Cα-arylate amides (α to nitrogen) and ethers using a variety of five- and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was revealed. This benzaldehyde-mediated photoredox reaction proceeded smoothly with household 23 W CFL bulbs as the energy source under metal-free conditions, allowing the construction of new Csp2–Csp2 and Csp3–Csp2 bonds and access to important pharmacophores of broad utility using commercially available reagents.

Graphical abstract: Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction

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Publication details

The article was received on 24 Sep 2015, accepted on 06 Dec 2015 and first published on 07 Dec 2015


Article type: Edge Article
DOI: 10.1039/C5SC03640B
Citation: Chem. Sci., 2016,7, 2111-2118
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    Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction

    Y. Zhang, K. B. Teuscher and H. Ji, Chem. Sci., 2016, 7, 2111
    DOI: 10.1039/C5SC03640B

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