4.8 Article

Curtius-like Rearrangement of an Iron-Nitrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes

Journal

ORGANIC LETTERS
Volume 18, Issue 9, Pages 2228-2231

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00864

Keywords

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Funding

  1. National Natural Science Foundation of China [21302193, 21572236]
  2. Natural Science Foundation of Yunnan Province [2014FA008, 2015FB167]
  3. Yunnan High-End Technology Professionals Introduction Program [2010CI117]
  4. program for changjiang scholars and innovative research team in university [IRT13095]

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A Curtius-like rearrangement of hydroxamates to isocyanates was discovered. This reaction was initiated from an iron(II)-nitrenoid complex, which was generated by the iron(II)-catalyzed cleavage of N-O bonds of functionalized hydroxamates. To demonstrate the efficiency of this new Curtius-like rearrangement in synthetic chemistry, a biomimetic strategy for the one-pot preparation of bisindolylmethanes was developed.

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