Brønsted acid-catalyzed reaction of alkynyltrifluoroborates with acetals and ketals
type: CreativeWork
description: The synthesis of small molecules is crucial in the pharmaceutical industry for producing drugs or biologically active compounds. Specifically, the formation of new carbon-carbon bonds is of great importance in synthetic organic chemistry. Brønsted acid catalysis is a powerful synthetic tool to make many different compounds, however, the current carbon-based nucleophiles are the major limitation of acid-catalyzed reactions. In effort to expand repertoire of Brønsted acid compatible nucleophiles, we present a novel carbon-carbon bond forming methodology between acetals, ketals, and potassium phenylacetylene trifluoroborate salts. Excellent functional group tolerance is observed with this protocol including, halogen, nitrile, nitro, acid and carbonyl functionalities.
abstract: The synthesis of small molecules is crucial in the pharmaceutical industry for producing drugs or biologically active compounds. Specifically, the formation of new carbon-carbon bonds is of great importance in synthetic organic chemistry. Brønsted acid catalysis is a powerful synthetic tool to make many different compounds, however, the current carbon-based nucleophiles are the major limitation of acid-catalyzed reactions. In effort to expand repertoire of Brønsted acid compatible nucleophiles, we present a novel carbon-carbon bond forming methodology between acetals, ketals, and potassium phenylacetylene trifluoroborate salts. Excellent functional group tolerance is observed with this protocol including, halogen, nitrile, nitro, acid and carbonyl functionalities.
author: Baxter, Matthew
language: en
keywords: Brønsted, Alkynyltrifluoroborates, Acetals, Ketals, Acid
date published: 2015-04-01
date modified: 2026-07-24T05:35:18Z
provider: Ontario Institute of Technology
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: University of Ontario Institute of Technology

PropertyValue
property ID: Handle
value: https://hdl.handle.net/10155/528