Visible light mediated regioselective 1,3-oxylallylation of aryl cyclopropanes under redox-neutral conditions

Pyridines and cyclopropanes are important structural units in chemistry. Herein, we introduce a photoredox-catalyzed approach for the ring opening and 1,3-oxypyridylation of aryl cyclopropanes using 4-cyanopyridines and carboxylic acids. This sequential process involves single-electron oxidation of the aryl cyclopropane, leading to nucleophilic ring opening and radical pyridylation at the benzylic position. The redox-neutral reaction exhibits high regioselectivity under mild reaction conditions, offering a broad substrate scope and wide applicability.

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Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent

Li,

Wu,

Song

et al. 2024

Nat Commun

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The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C–N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N -heterocyclic carbene (NHC), N -benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane. NHCs play multiple roles, functioning as Lewis base catalysts to activate C–N bonds, promoting the oxidative quenching process of PC*, and acting as efficient acyl radical transfer catalysts for the formation of C–C bonds. The oxidative quenching process between the excited-state PC* and acyl NHC adduct is the key to the photooxidation generality of aryl cyclopropanes.

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Visible light mediated regioselective 1,3-oxylallylation of aryl cyclopropanes under redox-neutral conditions

Abstract: A photoredox catalysed 1,3-oxylallylation of aryl cyclopropanes was accomplished by reaction with carboxylic acid and allyl sulfone. The redox-neutral reaction proceeded in a highly regioselective manner under mild conditions with...

Cited by 5 publications

References 54 publications

Photoinduced rapid Chloropropylation of Quinoxalin-2(1H)-ones with Cyclopropane and HCl

Photoinduced rapid Chloropropylation of Quinoxalin-2(1H)-ones with Cyclopropane and HCl

Photocatalytic Regioselective Redox-Neutral 1,3-Oxypyridylation of Aryl Cyclopropanes

Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent

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