Visible light C–H amidation of heteroarenes with benzoyl azides

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Visible light C-H amidation of heteroarenes with benzoyl azides.

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 he...

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Visible light C–H amidation of heteroarenes with benzoyl azides† †Electronic supplementary information (ESI) available: Characterization and synthesis of new compounds, general procedures, proton and carbon NMR spectra, crystal structure analysis, gas chromatographic analyses. CCDC 1017661. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02365j Click here for additional data file. Click here for additional data file.

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-, heteroarylor alkenyl acyl azides and has a wide scope for hete...

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A simple base-mediated amidation of aldehydes with azides.

A practical and efficient amidation reaction involving aromatic aldehydes and various azides under mild conditions is described. A broad spectrum of functional groups was tolerated, and the amides were synthesized in moderate to excellent yields, presenting an attractive alternative to the currently available synthetic methods.

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Sulfonylative and Azidosulfonylative Cyclizations by Visible‐Light‐Photosensitization of Sulfonyl Azides in THF

The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of THF as the solvent is critical for successful reactions. The proposed mechanism of radical initiat...

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A catalytic and tert-butoxide ion-mediated amidation of aldehydes with para-nitro azides.

We report here a new catalytic reaction in which, para-nitro azides are acylated by aldehydes to produce amides and molecular nitrogen in a single step. The transformation is believed to proceed via an electron transfer process mediated by the tert-butoxide ion, and catalysed by a thiazolium salt derived species.

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ژورنال

عنوان ژورنال: Chemical Science

سال: 2015

ISSN: 2041-6520,2041-6539

DOI: 10.1039/c4sc02365j