Electronic Influences on the Dynamic Range of Photoswitchable Dithienylethene-Thiourea Organocatalysts.
J Org Chem
; 88(7): 4372-4378, 2023 Apr 07.
Article
in En
| MEDLINE
| ID: mdl-36939093
ABSTRACT
Thiourea-based organocatalysts bearing a photoswitchable dithienylethene (DTE) core and a wide range of substituents were prepared and extensively tested for their ability to accelerate the Michael reaction between acetylacetone and trans-ß-nitrostyrene. There is a strong correlation between the Hammett parameter of the modulating groups and catalytic activity following UV irradiation. Electron-withdrawing groups afford the largest reactivity difference between the catalysts in their ring-open form and their ring-closed isomer, with evidence for electronic coupling between the two halves in both oDTE and cDTE.
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1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2023
Document type:
Article
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