Issue 3, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Sep 2015
Accepted
06 Dec 2015
First published
07 Dec 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 2111-2118

Author version available

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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