Photoinduced liberation of a phosphazene superbase as an initiator for oxa-Michael addition reactions

Abstract We describe herein the facile preparation and characterization of new photobase generators based on carboxylate-functionalized chromophores. They pair high wavelength absorption with the liberation of an extremely strong phosphazene superbase. We additionally demonstrate their outstanding capacity in initiating a Brønsted base mediated oxa-Michael addition through a systematic optimization study. To the best of our knowledge, this work marks the first report on the light triggered initiation of an oxa-Michael addition reaction between an alcohol and acrylamide via photobase generators. Graphical abstract

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Publication Details

Journal
Monatshefte für Chemie - Chemical Monthly
Published
2025-09-23
DOI
https://doi.org/10.1007/s00706-025-03378-6
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photoinduced liberation of a phosphazene superbase as an initiator for oxa-Michael addition reactions

Patrick Knaack, Robert Liska, Klaus Ableidinger, Edma Gjata
Monatshefte für Chemie - Chemical Monthly
Fluorine in Organic Chemistry
article

Photoinduced liberation of a phosphazene superbase as an initiator for oxa-Michael addition reactions

Patrick Knaack, Robert Liska, Klaus Ableidinger, Edma Gjata
article en

Abstract

Abstract We describe herein the facile preparation and characterization of new photobase generators based on carboxylate-functionalized chromophores. They pair high wavelength absorption with the liberation of an extremely strong phosphazene superbase. We additionally demonstrate their outstanding capacity in initiating a Brønsted base mediated oxa-Michael addition through a systematic optimization study. To the best of our knowledge, this work marks the first report on the light triggered initiation of an oxa-Michael addition reaction between an alcohol and acrylamide via photobase generators. Graphical abstract

Monatshefte für Chemie - Chemical MonthlyVol. 157(3)
TU Wien (AT)
Openalex Percentile: Top 80%
Fluorine in Organic Chemistry
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