4.5 Article

An Efficient Route to Quinolines and Other Compounds by Iron-Catalysed Cross-Dehydrogenative Coupling Reactions of Glycine Derivatives

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 8, Pages 1583-1589

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101656

Keywords

Natural products; Amino acids; Nitrogen heterocycles; Iron; Cross-coupling; Oxidation

Funding

  1. Important National Science & Technology Specific Projects, China [2009ZX09301-14-1]
  2. National Natural Science Foundation of China (NSFC) [21102107]
  3. Chinese Postdoctoral Science Foundation [20110491199]

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A simple method has been developed for functionalizing glycine derivatives by iron-catalysed cross-dehydrogenative coupling (CDC) reactions. In particular, N-arylglycine derivatives reacted with alkynes by oxidative CH/CH coupling reactions to provide a series of substituted quinolines starting from commercially inexpensive materials. Moreover, N-arylglycine esters can be oxidatively coupled to ketones by using FeCl3 in the presence of DDQ.

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