Visible‐Light‐Mediated Photocatalytic Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation/Semipinacol Rearrangement

Bergonzini, Giulia; Cassani, Carlo; Lorimer-Olsson, Haldor; Hörberg, Johanna; Wallentin, Carl‐Johan

doi:10.1002/chem.201504985

Cited by 90 publications

(31 citation statements)

References 70 publications

(19 reference statements)

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“…Wallentin and co‐workers in another work used anhydrides as acyl radical equivalents for the synthesis of ketones (Scheme ) . The work involved difunctionalization of olefins via radical acyl arylation and tandem acylation/semipinacol rearrangement to synthesise 3,3‐disubstituted 2‐oxindoles and 1,4‐diketones initiated by a single‐electron reduction of symmetric aromatic carboxylic anhydrides using fac‐[Ir(ppy) 3 ] as photocatalyst.…”

Section: Ketone Synthesis Using Iridium (Ir) Based Photocatalystsmentioning

confidence: 99%

Recent Advances in Photoredox Methods for Ketone Synthesis

2020

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Synthesis of ketones is one of the most addressed problems in organic chemistry owing to their presence in a diverse array of drugs, pharmaceuticals, natural products and photosensitizers. Many of the limitations associated with the traditional approaches enabling the synthesis of ketones like creation of high energy acylating reagents, poor functional group tolerance, pre-activation of starting materials have been largely addressed with the advent of photoredox chemistry. This review summarizes the recent advances made in the photoredox catalyzed synthesis of ketones. 2 3 4 5 6 7 8

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Section: Ketone Synthesis Using Iridium (Ir) Based Photocatalystsmentioning

confidence: 99%

Recent Advances in Photoredox Methods for Ketone Synthesis

2020

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“…employed aromatic carboxylic anhydride as the direct acyl radical source for olefinic radical acylarylation under photocatalytic conditions. 73 The method efficiently yielded substituted 3,3-disubstituted 2-oxindoles (45–98%) using a variety of symmetrical electron-withdrawing aromatic anhydrides. This protocol was also applied to variously substituted N -phenylacrylamides, obtaining products in 80–98% yields (Scheme 73).…”

Section: Anhydrides As a Source Of Acyl Radicalsmentioning

confidence: 99%

Acyl Radical Chemistry via Visible-Light Photoredox Catalysis

2018

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Visible light photoredox catalysis has enabled easy access to acyl radicals under mild reaction conditions. Reactive acyl radicals, generated from various acyl precursors such as aldehydes, α-ketoacids, carboxylic acids, anhydrides, acyl thioesters, acyl chlorides, or acyl silanes, can undergo a diverse range of synthetically useful transformations, which were previously difficult or inaccessible. This review summarizes such recent progress of visible-light-driven acyl radical generation using transition metal photoredox catalysts, metallaphotocatalysts, hypervalent iodine catalysts or organic photocatalysts.

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“…demonstrated av isible-light-promoted difunctionalization of TMS-protected allylic alcohols 24 by tandem acylation/semipinacol-type rearrangement reaction (Scheme 6a). [19] This protocol used benzoica nhydride as an acyl radical source and provides convenient access to 1,4-dicarbonyl compounds 25 in moderate to excellent yields. Ar easonable reactionm echanism for this transformationi ss hown in Scheme6b.…”

Section: Acyl Radicalsmentioning

confidence: 99%

“…Scheme6.Synthesis of 1,4-dicarbonylc ompounds by visible-light-promoted tandem acylation/semipinacol-type rearrangement of allylic alcohols by using benzoicanhydride as aacyl radical precursor.Adaptedf rom reference [19]. thylthiolation/semipinacol-type rearrangement of allylic alcohols 34 with N-(trifluoromethylthio)phthalimide as aS CF 3 radical source (Scheme 8a).…”

Section: Trifluoromethylthiyl Radicalsmentioning

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 Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation/Semipinacol Rearrangement

Cited by 90 publications

References 70 publications

Recent Advances in Photoredox Methods for Ketone Synthesis

Recent Advances in Photoredox Methods for Ketone Synthesis

Acyl Radical Chemistry via Visible-Light Photoredox Catalysis

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

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