Formation of Four Different Aromatic Scaffolds from Nitriles through Tandem Divergent Catalysis†
Dr. Ju Hyun Kim
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)
Search for more papers by this authorProf. Jean Bouffard
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)
Search for more papers by this authorCorresponding Author
Prof. Sang-gi Lee
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)Search for more papers by this authorDr. Ju Hyun Kim
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)
Search for more papers by this authorProf. Jean Bouffard
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)
Search for more papers by this authorCorresponding Author
Prof. Sang-gi Lee
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)
Department of Chemistry and Nano Science (BK 21 plus), Ewha Womans University, Seoul 120-750 (Korea)Search for more papers by this authorThis work was financially supported by the Korea Research Foundation (NRF-2011-0016344 and NRF-2009-0083525). We thank Dr. Y. Kim for X-ray analysis and the Daegu branch of the Korea Basic Science Research Center for mass spectrometric analyses.
Graphical Abstract
Four roads diverged: A zinc bromide complex, generated by the sequential reaction of nitriles with a Reformatsky reagent and 1-alkynes, is used as an intermediate for divergent palladium-catalyzed reactions. The reaction pathway depends on the choice of reaction solvents and palladium catalysts. The method provides a simple and efficient approach to four different frameworks starting from readily available nitriles.
Abstract
A zinc bromide complex, formed by the sequential reaction of nitriles with a Reformatsky reagent and terminal alkynes, is used as an intermediate for divergent palladium-catalyzed reactions. The reaction pathway of the intermediate is precisely controlled by the choice of the reaction solvent or the palladium catalyst to quickly form four different aromatic scaffolds—arylamines, aminoindenes, pyrroles, and quinolines—starting from readily available nitriles.
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