Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 10, Pages 2013-2022Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101816
Keywords
Nitrogen heterocycles; Fused-ring systems; Click reaction; Homogeneous catalysis; Copper; C-H activation; Arylation
Categories
Funding
- Department of Science and Technology (DST), New Delhi
- Council of Scientific and Industrial Researc (CSIR), New Delhi
- DST
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A sequential copper-catalyzed, one-pot, click reactionintramolecular direct arylation, which involves two mechanistically distinct reactions (atom-economical click reaction and direct arylation of 1,2,3-triazole), to generate [6,6]-, [6,7]-, [6,8]-, and [6,9]ring-fused triazoles is reported. Furthermore, a unique divergence of reactivity between the fused triazoles prepared from 2-bromobenzyl azide and 2-bromophenylazide that leads to a fused pentacyclic heterocycle for the former and a CC-coupled, biphenyl-fused, tricyclic product for the latter is observed under Pd catalysis. All of the key products have been characterized by single-crystal X-ray crystallography.
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