[2.2]Paracyclophane-based coumarins: effective organophotocatalysts for light-induced desulfonylation processes

19 October 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we demonstrate for the first time that coumarins derived from [2.2]paracyclophane (pCp) can act as effective organophotocatalysts and promote the reductive cleavage of sulfonamides under light-irradiation. In the presence of these original compounds, photodesulfonylation reactions occur under mild conditions at low catalyst loadings in the presence of Hantzsch ester. Theoretical and experimental investigations are described, which elucidate the reaction mechanism and the nature of the active species involved in the photocatalytic process. This proof-of-concept study paves the way for further application of pCps in the field of photocatalysis.

Keywords

[2.2]paracyclophanes
photodesulfonylations
coumarins
light-promoted processes

Supplementary materials

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Supporting information
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Electronic Supplementary Information (ESI) is available and includes: synthetic procedures for the preparation of all products, UV-vis absorption, fluorescence emission spectra, and cyclic voltammograms of the reaction partners, details on the photochemical apparatus, characterization data, theoretical data, copies of 1H NMR and 13C NMR spectra for all the synthesized compounds.
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