Red Light-Blue Light Chromoselective C(sp2)-X Bond Activation by Organic Helicenium-Based Photocatalysis.
J Am Chem Soc
; 146(12): 7922-7930, 2024 Mar 27.
Article
em En
| MEDLINE
| ID: mdl-38498938
ABSTRACT
Chromoselective bond activation has been achieved in organic helicenium (nPr-DMQA+)-based photoredox catalysis. Consequently, control over chromoselective C(sp2)-X bond activation in multihalogenated aromatics has been demonstrated. nPr-DMQA+ can only initiate the halogen atom transfer (XAT) pathway under red light irradiation to activate low-energy-accessible C(sp2)-I bonds. In contrast, blue light irradiation initiates consecutive photoinduced electron transfer (conPET) to activate more challenging C(sp2)-Br bonds. Comparative reaction outcomes have been demonstrated in the α-arylation of cyclic ketones with red and blue lights. Furthermore, red-light-mediated selective C(sp2)-I bonds have been activated in iodobromoarenes to keep the bromo functional handle untouched. Finally, the strength of the chromoselective catalysis has been highlighted with two-fold functionalization using both photo-to-transition metal and photo-to-photocatalyzed transformations.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article