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. 2015 Feb 1;6(2):987-992.
doi: 10.1039/c4sc02365j. Epub 2014 Oct 30.

Visible light C-H amidation of heteroarenes with benzoyl azides

E Brachet  1 , T Ghosh  1 , I Ghosh  1 , B König  1
Affiliations

Visible light C-H amidation of heteroarenes with benzoyl azides

E Brachet et al. Chem Sci. .

Abstract

Benzoyl azides were used for the direct and atom economic C-H amidation of electron rich heteroarenes in the presence of phosphoric acid, a photocatalyst and visible light. Hetero-aromatic amides are obtained in good yields at very mild reaction conditions with dinitrogen as the only by-product. The reaction allows the use of aryl-, heteroaryl- or alkenyl acyl azides and has a wide scope for heteroarenes, including pyrroles, indole, furan, benzofuran and thiophene giving good regio-selectivities and yields.

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Figures

Scheme 1
Scheme 1. Catalytic aromatic amidation reactions.
Scheme 2
Scheme 2. Synthesis of compound 6 using photocatalytic C–H amidation with benzoyl azide 1g.
Scheme 3
Scheme 3. Isolated oxazolines from the photoreaction.
Scheme 4
Scheme 4. Proposed mechanism of the photo CH-amidation of benzofuran with benzoyl azide in the presence of acid, Ru(bpy)3Cl2 and blue light.
See this image and copyright information in PMC

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