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Synfacts 2022; 18(12): 1343
DOI: 10.1055/s-0042-1752361
Polymer-Supported Synthesis

Photochemical Giese Reaction of Dioxolane and Vinyl Ketones on Graphitic Carbon Nitride

Rezensent(en):
Yasuhiro Uozumi
,
Ryoko Niimi
Gerken VC, Carreira EM. * ETH Zürich, Switzerland
Carbon Nitride Photoredox Catalysis Enables the Generation of the Dioxolanyl Radical for Conjugate Addition Reactions.

ACS Catal. 2022;
12: 10787-10792
DOI: 10.1021/acscatal.2c03229
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Key words

carbon nitride - photocatalysis - Giese reaction - dioxolane - vinylic ketones

Significance

Graphitic carbon nitride ( g-C3N4 ), prepared by thermal condensation of dicyandiamide (eq. 1), catalyzed the Giese reaction of 1,3-dioxolane with vinyl ketones under blue LED irradiation (λ = 466 nm) for 12–24 hours to give the corresponding products in ≤99% yield (eq. 2).


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Comment

In the Giese reaction of 1,3-dioxolane with diethyl fumarate, g-C3N4 was reused four times without a significant loss of its catalytic activity. SEM, FT-IR, XRD, UV/vis, and elemental (C, N, and H) analyses of the used catalyst revealed that its morphology remained intact during the reaction.


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Publikationsverlauf

Artikel online veröffentlicht:
17. November 2022

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