4.6 Article

tert-Butyl Nitrite Mediated Regiospecific Nitration of (E)-Azoarenes through Palladium-Catalyzed Directed C-H Activation

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 32, Pages 9862-9866

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403325

Keywords

C-H activation; nitration; o-nitroazoarenes; palladium; tert-butyl nitrite

Funding

  1. DST, Govt. of India, New Delhi [SR/S2/JCB-11/2008]
  2. CSIR, New Delhi
  3. DBT [BT/01/CEIB/11V/13]

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An efficient protocol for the Pd-catalyzed regiospecific ortho-nitration of (E)-azoarenes has been achieved for the first time using tBuONO as a nitrating agent under atmospheric oxygen. A series of both symmetrical and unsymmetrical azoarenes were nitrated efficiently by this procedure providing excellent chemo-and regioselectivity and compatibility with a broad array of functional groups.

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