909104-05-8Relevant articles and documents
Predictable and site-selective functionalization of poly(hetero)arene compounds by palladium catalysis
Lapointe, David,Markiewicz, Thomas,Whipp, Christopher J.,Toderian, Amy,Fagnou, Keith
experimental part, p. 749 - 759 (2011/04/16)
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-Hfunctionalization 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.
