Predictable and Site-Selective Functionalization of Poly(hetero)arene Compounds by Palladium Catalysis
Citations Over TimeTop 10% of 2010 papers
Abstract
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.
Related Papers
- → First Regioselective Ortho-Lithiation Induced by a 2-Chloropyridyl Group Complexation(2003)34 cited
- → Regioselective formylation of 1,3-disubstituted benzenes through in situ lithiation(2013)11 cited
- → The First Regioselective Metalation and Functionalization of Unprotected 4-Halobenzoic Acids(2005)26 cited
- → Metalation of diazines XVII Very hindered bases as new metalating agents, Improvement of regioselectivity for the metalation of 3-chloro-6-methoxypyridazine(1996)23 cited
- → Regioselectivity in the Lithiation ofO-(4-Methoxyphenyl)-N,N-diethylthiocarbamate: Relative Directed Metalation Abilities of Methoxy and N,N-diethylthiocarbamate Functionalities(1997)3 cited