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J Org Chem. 2011 Feb 4;76(3):749-59. doi: 10.1021/jo102081a. Epub 2010 Dec 1.

Predictable and site-selective functionalization of poly(hetero)arene compounds by palladium catalysis.

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Center for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, ON, Canada.


The challenge of achieving selective and predictable functionalizations at C-H bonds with complex poly(hetero)aromatic substrates was addressed by two different approaches. Site-selectivity can be obtained by applying various reaction conditions that are (hetero)arene specific to substrates that contain indoles, pyridine N-oxide, and polyfluorinated benzenes. An experimental classification of electron-rich heteroarenes based on their reactivity toward palladium-catalyzed C-H functionalization was established, the result of which correlated well with the order of reactivity predicted by the DFT-calculated concerted metalation-deprotonation (CMD) pathway. Model substrates containing two reactive heteroarenes were then reacted under general reaction conditions to demonstrate the applicability this reactivity chart in predicting the regioselectivity of the palladium-catalyzed direct arylation and benzylation reactions.

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