Internal Lewis Acid Assisted Single Hydrogen Bond Donor Catalysis
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Date
2011-06
Authors
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Publisher
The Ohio State University
Abstract
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid has been identified as a new single
hydrogen bond donor organic catalyst for the addition of indole to β-nitrostyrene. This catalyst
offers enhanced reactivity over other benzoic acid derivatives lacking the boron substituent and it
was reasoned this benefit results from the internal coordination the Lewis acid to the carboxylic
acid functionality causing an increase in the acidity and improvement in catalyst function. Key
features of 2-boryl benzoic acid catalysts making them particularly attractive include: their ease
of preparation, shelf stability and convenience of use.
Description
Keywords
hydrogen bond catalysis, organic catalysis, non-covalent catalysis, silicon catalyst, boron catalyst