Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8632 - 8640

Опубликована: Июнь 6, 2024

Herein, we disclosed a highly efficient pathway toward 3-selenylated chromone derivatives via electrocatalytic cascade selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amendable to scale-up the reaction. Additionally, preliminary experiments revealed that reaction probably proceeded cation instead radical pathway.

Язык: Английский

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Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3670 - 3675

Опубликована: Июль 2, 2024

Abstract With an in situ C−H iodination tactic, a method for the synthesis of chromone‐3‐phosphonates was developed with trialkyl/triaryl phosphites as reaction partners o ‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists cascade iodination, chromone annulation, and Arbuzov‐type C−P cross coupling major transformations. In addition to providing enaminone‐based synthetic chromone‐3‐phosphonates, work shows advantage step economy skipping separate operation preparing iodo‐functionalized intermediate.

Язык: Английский

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Copper-Catalyzed Enaminone C(sp²)–N Bond Phosphonation for Stereoselective Synthesis of Alkenylphosphonates

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(14), С. 9861 - 9868

Опубликована: Июнь 30, 2021

A direct enaminone C–N bond coupling functionalization that generates a new C–P using dialkyl phosphonate for the efficient and stereoselective synthesis of (E)-alkenylphosphonates is reported. The reactions toward target products proceed well with broad scope, disclosing valuable synthetic application enaminones by interesting C(sp2)–N elaboration.

Язык: Английский

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Transition‐Metal‐Free C(sp²)−H Phosphorothiolation/Cyclization of o‐Hydroxyarylenaminones: Access to S‐3‐Chromon Phosphorothioates

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(9), С. 1602 - 1606

Опубликована: Март 19, 2022

Abstract The C( sp 2 )−H phosphorothiolation involving cyclization process through a transition‐metal‐free strategy is reported. It provides an attractive approach for the construction valuable S ‐3‐chromon phosphorothioates from o ‐hydroxyarylenaminones and P(O)SH compounds in presence of 1.0 equiv. iodine at 60 °C. This novel protocol shows readily available chemicals, broad substrate scope, mild reaction conditions. magnified image

Язык: Английский

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Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o-hydroxyaryl enaminones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(46), С. 9236 - 9241

Опубликована: Янв. 1, 2023

A convenient and efficient method for the synthesis of difluoro/trifluoromethyl carbinol-containing chromone derivatives has been developed.

Язык: Английский

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