Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 3, Pages 749-759Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo102081a
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Funding
- NSERC
- University of Ottawa
- Eli Lilly
- Amgen
- Astra Zeneca
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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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