4.8 Article

Visible-Light-Promoted Redox Neutral C-H Amidation of Heteroarenes with Hydroxylamine Derivatives

Journal

ORGANIC LETTERS
Volume 16, Issue 13, Pages 3504-3507

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol501457s

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Funding

  1. 863 program [2013AA092903]
  2. National Natural Science Foundation of China [21272113]
  3. Natural Science Foundation of Jiangsu Province [BK20131266]

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A room temperature redox neutral direct C H amidation of heteroarenes has been achieved. Hydroxylamine derivatives, which are easily accessed, have been employed as tunable nitrogen sources. These reactions were enabled by a visible-light-promoted single-electron transfer pathway without a directing group. A variety of heteroarenes, such as indoles, pyrroles, and furans, could go through this amidation with high yields (up to 98%). These reactions are highly regioselective, and all the products were isolated as a single regioisomer.

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