Visible-light-mediated photocatalytic difluoroalkylation/1,2-carbon migration sequences: synthesis of difluoroalkyl-substituted cyclic ketones

Suh, Chang Won; Kim, Dae Young

doi:10.1016/j.tetlet.2015.08.068

Cited by 54 publications

(14 citation statements)

References 87 publications

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“…Even though alkenyl cyclobutanols are effective radical acceptors in these radical-mediated semipinacol-type rearrangements, competing epoxide formation has motivated chemists to design more general substrates. In 2015, the Kim group utilized silyl-protected alkenyl cyclobutanols as radical acceptors and achieved a photocatalytic ethoxycarbonyldifluoromethylation/1,2-carbon migration . A short time later, they developed a bis(alkoxycarbonyl)methylation/1,2-carbon migration of silyl-protected alkenyl cyclobutanols .…”

Section: Miscellaneousmentioning

confidence: 99%

“…In 2015, the Kim group utilized silyl-protected alkenyl cyclobutanols as radical acceptors and achieved a photocatalytic ethoxycarbonyldifluoromethylation/ 1,2-carbon migration. 270 A short time later, they developed a bis(alkoxycarbonyl)methylation/1,2-carbon migration of silylprotected alkenyl cyclobutanols. 271 These reactions showed good functional group tolerance and broad substrate scope.…”

Section: Radical Migration-mediated C−c Bond Cleavagementioning

confidence: 99%

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Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis

2020

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Thermal C−C bond cleavage reactions allow the construction of structurally diverse molecular skeletons via predictable and efficient bond reorganizations. Visible light photoredox-catalyzed radical-mediated C−C bond cleavage reactions have recently emerged as a powerful alternative method for overcoming the thermodynamic and kinetic barrier of C−C bond cleavage in diverse molecular scaffolds. In recent years, a plethora of elegant and useful reactions have been invented, and the products are sometimes otherwise inaccessible by classic thermal reactions. Considering the great influence and synthetic potential of these reactions, we provide a summary of the state of art visible light-driven radical-mediated C−C bond cleavage/functionalization strategies with a specific emphasis on the working models. We hoped that this review will be useful for medicinal and synthetic organic chemists and will inspire further reaction development in this interesting area.

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Section: Miscellaneousmentioning

confidence: 99%

Section: Radical Migration-mediated C−c Bond Cleavagementioning

confidence: 99%

Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis

2020

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“…As part of our ongoing research program on the C–H bond activation, we recently presented the radical‐mediated functionalization of alkenes and aromatics . Herein, we report on the transition metal‐free oxidative phosphorylation of vinyl azides with phosphine oxides.…”

Section: Methodsmentioning

confidence: 99%

Transition Metal‐free Phosphorylation of Vinyl Azides: A Convenient Synthesis of β‐Ketophosphine Oxides

Jang

Kim

2020

Bulletin Korean Chem Soc

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“…[17] Various functional groups are tolerateda nd the corresponding b-difluoromethylated cyclic ketones 23 were prepared in moderate to good yields.M echanistic studies revealed that CF 2 CO 2 Et radicals are reactioni ntermediates in these transformations. [17] Various functional groups are tolerateda nd the corresponding b-difluoromethylated cyclic ketones 23 were prepared in moderate to good yields.M echanistic studies revealed that CF 2 CO 2 Et radicals are reactioni ntermediates in these transformations.…”

Section: Fluoroalkylradicalsmentioning

confidence: 99%

Recent Advances in the Synthesis of β‐Functionalized Ketones by Radical‐Mediated 1,2‐Rearrangement of Allylic Alcohols

Weng

Zhang

2018

Chemistry A European J

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β-Functionalized ketones are a highly important and valuable class of compounds that have gained increasing attention from organic chemists due to their intensive uses as versatile synthetic intermediates and building blocks in complex molecule assembly and natural product synthesis. Accordingly, there is continuing interest in the development of new approaches for the synthesis of β-functionalized ketones. In recent years, radical-mediated 1,2-rearrangement reactions of allylic alcohols, which proceed through cationic (semipinacol) rearrangements or radical (neophyl) rearrangements, have presented an attractive and powerful strategy to access various diversely β-functionalized ketones. Interestingly, this strategy allows for the direct installation of a variety of valuable functional groups at the β-position of cyclic and acyclic ketones by employing different radical precursors. However, a review focusing on the preparation of β-functionalized ketones by radical-mediated 1,2-rearrangement reactions of allylic alcohols has not been summarized to date. This Minireview highlights recent progress made in this highly active and interesting research area, and the corresponding mechanisms will also be discussed.

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Visible-light-mediated photocatalytic difluoroalkylation/1,2-carbon migration sequences: synthesis of difluoroalkyl-substituted cyclic ketones

Cited by 54 publications

References 87 publications

Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis

Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis

Transition Metal‐free Phosphorylation of Vinyl Azides: A Convenient Synthesis of β‐Ketophosphine Oxides

Recent Advances in the Synthesis of β‐Functionalized Ketones by Radical‐Mediated 1,2‐Rearrangement of Allylic Alcohols

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