Visible light-mediated arylalkylation of allylic alcohols through concomitant 1,2-aryl migration

Huang, Han-Ching; Hao, Yan; Yang, Chao; Xia, Wujiong

doi:10.1039/c4cc10321a

Cited by 54 publications

(21 citation statements)

References 56 publications

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“…This domino process involved the formation of an alkylnitrile radical, its intramolecular addition to the C=C double bond, followed by 1,2-aryl migration and generation of a carbonyl group, as main steps (Scheme 8). Starting from similar allylic alcohols Xia et al proposed a visible light-promoted radical arylalkylation with diethyl bromomalonate [27]. Optimization of the reaction conditions evidenced fac-Ir(ppy)3 as the best photoredox catalyst in DMSO, in the presence of 2,6-lutidine as additive (Scheme 9).…”

Section: Sp 3 C-centered Radical-promoted Rearrangementsmentioning

confidence: 99%

“…The potential application of this approach was demonstrated by a formal synthesis of (±)-sequirin D, a norlignan-type natural product with anti-gonadotropic activity. Starting from similar allylic alcohols Xia et al proposed a visible light-promoted radical arylalkylation with diethyl bromomalonate [27]. Optimization of the reaction conditions evidenced fac-Ir(ppy) 3 as the best photoredox catalyst in DMSO, in the presence of 2,6-lutidine as additive (Scheme 9).…”

Section: Sp 3 C-centered Radical-promoted Rearrangementsmentioning

confidence: 99%

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Radical Smiles Rearrangement: An Update

2016

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Over the decades the Smiles rearrangement and its variants have become essential synthetic tools in modern synthetic organic chemistry. In this mini-review we summarized some very recent results of the radical version of these rearrangements. The selected examples illustrate the synthetic power of this approach, especially if it is incorporated into a domino process, for the preparation of polyfunctionalized complex molecules.

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Section: Sp 3 C-centered Radical-promoted Rearrangementsmentioning

confidence: 99%

Section: Sp 3 C-centered Radical-promoted Rearrangementsmentioning

confidence: 99%

Radical Smiles Rearrangement: An Update

2016

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“…In 2015, Xia and co‐workers described the first visible‐light‐mediated arylalkylation of alkenes (Scheme 27). [28] Similar to the work described by Zhu and co‐workers, [22] this reaction proceeds through a radical addition/1,2‐aryl migration process and can be used to synthesize various α‐aryl‐β‐alkylated ketones. In this case, polyfluorohalogenated radical precursors have been switched to bromomalonate, allowing the formation of a malonyl radical.…”

Section: C−c Bond Formationmentioning

confidence: 86%

Spotlight on Photoinduced Aryl Migration Reactions

Huynh

Abreu

Belmont

et al. 2020

Chemistry A European J

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Rearrangement reactions are certainly one of the most useful approaches towards complex structures in organic chemistry. With efficient conditions, it is indeed possible to convert simple substrates into highly functionalized products. Moreover, combining this approach with an attractive initiation process, such as visible‐light catalysis, makes these reactions particularly powerful. Recently, tremendous improvements have been made, owing to a better understanding of photoredox mechanisms. In this review, recent progress on visible‐light aryl migration reactions is discussed, focusing especially on Smiles rearrangement and related reactions.

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“…Synthesis of 1,5-dicarbonyl compoundsbyv isible-light-promoted alkylation-initiated radical 1,2-aryl migration of allylic alcohols.Adapted from references [30,31]. Ap ossible mechanism is showedi nS cheme 15 b.…”

Section: Alkyl 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 arylalkylation of allylic alcohols through concomitant 1,2-aryl migration

Cited by 54 publications

References 56 publications

Radical Smiles Rearrangement: An Update

Radical Smiles Rearrangement: An Update

Spotlight on Photoinduced Aryl Migration Reactions

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

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