4.6 Article

Bridging C-H Activation: Mild and Versatile Cleavage of the 8-Aminoquinoline Directing Group

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 47, Pages 16804-16807

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604344

Keywords

8-aminoquinoline; C-H activation; cleavage; directing group; ozonolysis

Funding

  1. graduate program MolTag (Austrian Science Fund FWF) [W1232]
  2. Fundacao para a Ciencia e Tecnologia [SFRH/BPD/100677/2014]
  3. ERASMUS program

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8-Aminoquinoline has emerged as one of the most powerful bidentate directing groups in history of C-H activation within the last decade. However, cleavage of its robust amide bond has shown to be challenging in several cases, thus jeopardizing the general synthetic utility of the method. To overcome this limitation, we herein report a simple oxidative deprotection protocol. This transformation rapidly converts the robust amide to a labile imide, allowing subsequent cleavage in a simple one-pot fashion to rapidly access carboxylic acids or amides as final products.

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