4.6 Article

Visible-Light-Induced Direct Oxidative C-H Amidation of Heteroarenes with Sulfonamides

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 44, Pages 15669-15673

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604014

Keywords

C-H amidation; heterocycles; nitrogen-centered radicals; photochemistry; visible light

Funding

  1. National Natural Science Foundation of China [21472084, 21572102, 81421091]

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A direct oxidative C-H amidation of heteroarenes with sulfonamides via nitrogen-centered radicals has been achieved. Nitrogen-centered radicals are directly generated from oxidative cleavage of N-H bonds under visible-light photoredox catalysis. Sulfonamides, which are easily accessed, are used as tunable nitrogen sources and bleach (aqueous NaClO solution) is used as the oxidant. A variety of heteroarenes, including indoles, pyrroles and benzofurans, can undergo this amidation with high yields (up to 92%). These reactions are highly regioselective, and all the products are isolated as single regioisomer.

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