4.8 Article

Oxidative Pd(II)-Catalyzed C-H Bond Amination to Carbazole at Ambient Temperature

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 48, Pages 16184-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja806543s

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Funding

  1. EPSRC [EP/D078180/1] Funding Source: UKRI
  2. Engineering and Physical Sciences Research Council [EP/D078180/1] Funding Source: researchfish

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We report a new Pd(II)-catalyzed C-H bond amination reaction to form carbazoles, an important motif that is prevalent in a range of systems. The catalytic amination process operates under extremely mild conditions and produces carbazole products in good to excellent yields, Carbazoles possessing complex molecular architecture can also be formed using this reaction, highlighting its potential in natural product synthesis applications. Preliminary mechanistic investigations reveal the reaction proceeds through a Pd(II)/Pd(IV) manifold and that reductive elimination from a high oxidation state Pd(IV) complex facilitates the mild conditions of this transformation.

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