Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 5, Pages 1592-1596Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504207
Keywords
amination; azo compounds; C-H activation; copper; homogeneous catalysis
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Funding
- CSIR New Delhi [02(0212)/14/EMR-II]
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A copper-catalyzed 8-amide chelation-induced remote C-H amination of quinolines has been developed. This direct amination with readily available azodicarboxylates proceeded with perfect C5-regioselectivity offering amino-substituted 8-aminoquinolines, important bioactive molecular scaffolds, in very high yields (up to 96 %). A single-electron transfer (SET)-mediated mechanism with k(H)/k(D)=1.1 was proposed after trapping of the radical intermediate.
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