Übergangsmetallfreie oxidative Kreuzkupplung von Tetraarylboraten zu Biarylen mit organischen Oxidationsmitteln

Gerleve, Carolin; Studer, Armido

doi:10.1002/ange.202002595

Cited by 6 publications

(2 citation statements)

References 71 publications

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“…Instead of electrochemical oxidation, Bobbitt’s salt ((4-(acetylamino)-2,2,6,6-tetramethyl-1-oxo-piperidinium tetrafluoroborate)) was employed as the one-electron oxidant. 28…”

Section: Other Reactions Involving the Zweifel Olefination Mechanismmentioning

confidence: 99%

Recent Progress on the Zweifel Olefination: An Update

Song,

2023

Synthesis

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During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. 1 Introduction 2 Zweifel Olefination with New Organometallic Species 3 Zweifel Olefination with New Migrating Groups 4 Electrochemical and Photocatalyzed Zweifel Olefination 5 New Elimination and Migration Patterns of Zweifel Olefination 6 Zweifel Olefination in Natural Product Synthesis 7 Other Reactions Involving the Zweifel Olefination Mechanism 8 Conclusions and Outlook

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“…Instead of electrochemical oxidation, Bobbitt’s salt ((4-(acetylamino)-2,2,6,6-tetramethyl-1-oxo-piperidinium tetrafluoroborate)) was employed as the one-electron oxidant. 28…”

Section: Other Reactions Involving the Zweifel Olefination Mechanismmentioning

confidence: 99%

Recent Progress on the Zweifel Olefination: An Update

Song,

2023

Synthesis

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“…The biphenyl is a widespread functional group that is integral to many natural products, [1] agrochemicals, [2] liquid crystals, [3] and pharmaceuticals. [4] The economic importance of biphenyls has led to the development of a variety of synthetic approaches, most notably the metal-dependent cross-coupling reaction (Figure 1A). [5] The major advantage compared over direct coupling is the superior regio-and chemoselectivity conferred by the metal catalyst.…”

Section: Introductionmentioning

confidence: 99%

Photosensitizers Enable the Formation of Biphenyls with UV‐LEDs and Sunlight

Haensch,

Hertweck

2024

Chemistry A European J

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The regioselective synthesis of biphenyls, which are economically important pharmaceuticals, agrochemicals, and liquid crystals, is a challenging task. Current methods rely on metal‐dependent cross‐coupling reactions, which unfortunately require the use of harmful halogenated aryls and heavy metal catalysts that are toxic and difficult to remove from the final products. Recently, we have circumvented these problems by developing a metal‐free and broadly applicable photochemical method for biphenyl synthesis using UV‐C light, called photosplicing. Here we present an improved method using photosensitizers in combination with UV‐B, UVA light, or sunlight. Using a high‐precision flow reactor with deep‐UV LEDs, we investigated the ability of commonly available organic photosensitizers to enhance the photosplicing reaction and identified a number of suitable photosensitizers with the required triplet energy. This method allows for easy batch synthesis of biaryls in borosilicate glassware and paves the way for their large‐scale production without the need for flow reactors.

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Oxoammonium Salt‐Mediated Vicinal Oxyazidation of Alkenes with NaN₃: Access to β‐Aminooxy Azides

Chen

Tang

et al. 2021

Adv Synth Catal

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An approach to the vicinal oxyazidation of alkenes has been achieved under mild and transition metal-free conditions. This method utilizes NaN 3 as the azidation agent and 2,2,6,6tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO + BF 4 À ) as the single-electron oxidant as well as the oxygen source. By using this protocol, various β-aminooxy azides were synthesized and several complex bioactive molecules were functionalized.

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Übergangsmetallfreie oxidative Kreuzkupplung von Tetraarylboraten zu Biarylen mit organischen Oxidationsmitteln

Cited by 6 publications

References 71 publications

Recent Progress on the Zweifel Olefination: An Update

Recent Progress on the Zweifel Olefination: An Update

Photosensitizers Enable the Formation of Biphenyls with UV‐LEDs and Sunlight

Oxoammonium Salt‐Mediated Vicinal Oxyazidation of Alkenes with NaN₃: Access to β‐Aminooxy Azides

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Übergangsmetallfreie oxidative Kreuzkupplung von Tetraarylboraten zu Biarylen mit organischen Oxidationsmitteln

Cited by 6 publications

References 71 publications

Recent Progress on the Zweifel Olefination: An Update

Recent Progress on the Zweifel Olefination: An Update

Photosensitizers Enable the Formation of Biphenyls with UV‐LEDs and Sunlight

Oxoammonium Salt‐Mediated Vicinal Oxyazidation of Alkenes with NaN3: Access to β‐Aminooxy Azides

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Oxoammonium Salt‐Mediated Vicinal Oxyazidation of Alkenes with NaN₃: Access to β‐Aminooxy Azides