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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Directed copper-catalyzed C-H functionalization of unactivated olefins with azodicarbonamide compounds
Jing Cui1, Xiaoya Wang1, Runsheng Zeng1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University Suzhou 215123 P. R. China zengrunsheng@suda.edu.cn.
Abstract:
The copper-catalyzed strategy employing the 8-aminoquinoline directing group has proven to be a highly advantageous approach for functionalizing C-H bonds. In this study, we present the successful application of this strategy to accomplish Heck-type coupling reactions and construct β-lactam skeletons, simultaneously introducing a unique cyano functional group. The resulting Heck-type coupling products demonstrate good stereo- and region-selectivity. Initial mechanistic investigations indicate that the reaction proceeds via a radical coupling mechanism, exhibiting a wide substrate scope and delivering good yields.
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