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Internal Lewis Acid Assisted Single Hydrogen Bond Donor Catalysis

Christopher Johnson-2011-06-01-The Knowledge Bank (The Ohio State University)

TL;DRAbstract

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid has been identified as a new single\nhydrogen bond donor organic catalyst for the addition of indole to β-nitrostyrene. This catalyst\noffers enhanced reactivity over other benzoic acid derivatives lacking the boron substituent and it\nwas reasoned this benefit results from the internal coordination the Lewis acid to the carboxylic\nacid functionality causing an increase in the acidity and improvement in catalyst function. Key\nfeatures of 2-boryl benzoic acid catalysts making them particularly attractive include: their ease\nof preparation, shelf stability and convenience of use.

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2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid has been identified as a new single\nhydrogen bond donor organic catalyst for the addition of indole to β-nitrostyrene. This catalyst\noffers enhanced reactivity over other benzoic acid derivatives lacking the boron substituent and it\nwas reasoned this benefit results from the internal coordination the Lewis acid to the carboxylic\nacid functionality causing an increase in the acidity and improvement in catalyst function. Key\nfeatures of 2-boryl benzoic acid catalysts making them particularly attractive include: their ease\nof preparation, shelf stability and convenience of use.

Keywords

CatalysisLewis acids and basesChemistryHydrogen bondHydrogenCombinatorial chemistryOrganic chemistryMolecule

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