Generation of Aryllithium Reagents from N-Arylpyrroles Using Lithium

Ozaki, Tomoya; Kaga, Atsushi; Saito, Hayate; Yorimitsu, Hideki

doi:10.1055/a-1482-2567

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An Alternative Synthesis Of 35-di-tert-butylphenyltrimethyls...1

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2022

2024

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Cited by 4 publications

(1 citation statement)

References 29 publications

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“…The NMR data were consistent with the reported values. 30 HRMS (APCI): m/z [M] + calcd for C 17 H 30 Si: 262.1117; found: 262.1114.…”

Section: An Alternative Synthesis Of 35-di-tert-butylphenyltrimethyls...mentioning

confidence: 99%

Synthesis of Phosphinoboranes via Coordination-Induced Bromine Abstraction of an Isolable Phosphinyl Radical with Bromoboranes

Ishida,

Iwamoto,

Katayama

et al. 2024

Synthesis

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A stable dialkylphosphinyl radical reacted with bromoboranes to afford the corresponding phosphinoboranes accompanied with a bromophosphine under neutral condition at room temperature. The obtained phosphinoboranes have almost planar structures and have an effective P–B dative π-bond. The formation of phosphinoboranes would proceed via coordination-induced bromine abstraction from bromoboranes as a pivotal step, which was supported by the computational study.

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“…The NMR data were consistent with the reported values. 30 HRMS (APCI): m/z [M] + calcd for C 17 H 30 Si: 262.1117; found: 262.1114.…”

Section: An Alternative Synthesis Of 35-di-tert-butylphenyltrimethyls...mentioning

confidence: 99%

Synthesis of Phosphinoboranes via Coordination-Induced Bromine Abstraction of an Isolable Phosphinyl Radical with Bromoboranes

Ishida,

Iwamoto,

Katayama

et al. 2024

Synthesis

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Preparation of Vinylic Lithium Reagents from Silyl Enolates of Alkyl Aryl Ketones Using Lithium Arenide

et al. 2023

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The preparation of vinylic lithium reagents from vinylic halides is a common practice in organic synthesis. However, the preparation of vinylic halides is not always straightforward. In this study, we propose the use of silyl enolates of alkyl aryl ketones as a readily available and efficient alternative for generating vinylic lithium species. Treatment of triisopropylsilyl enolates of alkyl aryl ketones with lithium naphthalenide or lithium 4,4’‐di‐t‐butylbiphenylide affords the corresponding vinylic lithium species. This preparation represents a reductive transformation of electron‐rich silyl enolates, which had remained unexplored. This process provides an alternative to the Shapiro reaction and has great potential for various applications in organic synthesis.

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Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles

2022

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Generation of Aryllithium Reagents from N-Arylpyrroles Using Lithium

Abstract: Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder at ambient temperature in THF results in the generation of the corresponding aryllithium reagents through reductive C-N bond cleavage.

Cited by 4 publications

References 29 publications

Synthesis of Phosphinoboranes via Coordination-Induced Bromine Abstraction of an Isolable Phosphinyl Radical with Bromoboranes

Synthesis of Phosphinoboranes via Coordination-Induced Bromine Abstraction of an Isolable Phosphinyl Radical with Bromoboranes

Preparation of Vinylic Lithium Reagents from Silyl Enolates of Alkyl Aryl Ketones Using Lithium Arenide

Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles

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