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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Synergistic Photoredox and Palladium-Catalyzed 1,3-Acyloxyallylation of Aryl Cyclopropanes with Allyl Esters

Ren,

Wei,

et al. 2024

ACS Catal.

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A synergistic photoredox and palladium-catalyzed 1,3-acyloxyallylation of aryl cyclopropanes with allyl esters has been developed. Aryl cyclopropanes are unprecedentedly employed as radical precursors in palladium-catalyzed allylation reactions with allyl esters acting as bifunctional reagents, thereby providing acyloxy groups as nucleophiles and the allyl moiety as a radical scavenger for the formation of benzylic C(sp 3 )−C(sp 3 ) bonds. This redox-neutral reaction exhibits 100% atom economy and good functional group tolerance and has been successfully applied to the late-stage modification of pharmaceutical derivatives.

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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 6 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

Synergistic Photoredox and Palladium-Catalyzed 1,3-Acyloxyallylation of Aryl Cyclopropanes with Allyl Esters

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