4.8 Article

Dehydrogenative N-Incorporation: A Direct Approach to Quinoxaline N-Oxides under Mild Conditions

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 39, Pages 10495-10499

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406479

Keywords

C-N bond formation; cyclization; dehydrogenative coupling; imines; nitrogen oxides

Funding

  1. National Natural Science Foundation of China [21325206, 21172006]
  2. National Young Top-notch Talent Support Program
  3. Ph.D. Programs Foundation of the Ministry of Education of China [20120001110013]

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An efficient method for the synthesis of quinoxaline N-oxides proceeds by the dehydrogenative N-incorporation of simple imines by C(sp(2))-H and C(sp(3))-H bond functionalization. The overall transformation involves the cleavage of three C H bonds. The reaction is easily handled and proceeds under mild conditions. Simple and readily available tert-butyl nitrite (TBN) was employed as the NO source.

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