Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 42, Pages 13692-13697Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403515
Keywords
amines; CN bond formation; copper; NN bond formation; triazoles
Categories
Funding
- National Basic Research Program of China [2011CB936003]
- Natural Science Foundation of China [21272205]
- Program for the Zhejiang Leading Team of Science and Technology Innovation [2011R50007]
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An effective copper-mediated synthesis of 1,5-dialkyl-4-aryl-1,2,3-triazoles and 1,4-dialkyl-5-aryl-1,2,3-triazoles has been achieved by the use of different N-tosylhydrazones and alkyl amines. The scope of the substrates could be extended from anilines to aliphatic amines when 30mol% amino acid is added into the reaction mixture. This methodology exhibits many notable features, such as broad substrates scope, high efficiency, and good regioselectivity. Preliminary mechanistic studies indicated that the reaction probably proceeded through a 1-tosyl-2-vinyldiazene intermediate and subsequent aza-Michael addition and NN bond formation process.
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