Regioselektive Allyl‐Allyl‐Kreuzkupplungen ohne Übergangsmetallkatalysator

A transition‐metal‐free approach to benzyl sulfones by using sodium sulfinates and benzyl ammonium salts is described. The protocol provides a simple and direct method to realize the C−N bond cleavage in the presence of readily available Cs2CO3. During the reaction process, a range of functional groups with respect to both sodium sulfinates and benzylic ammonium salts were well compatible, leading to various benzyl sulfones in moderate to good yields.

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Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

Liu

Zhu

Liu

et al. 2020

Asian J Org Chem

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Hoch regioselektive Addition von allylischen Zinkhalogeniden und verschiedenen Zinkenolaten an [1.1.1]Propellan

et al. 2020

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Wirb erichten über eine Reihe von hochregioselektiven Öffnungen von [1.1.1]Propellan mit verschiedenen allylischen Zinkhalogeniden, sowie mit Zinkenolaten von Ketonen, Estern und Nitrilen. Die resultierenden zinkierten Bicyclopentane (BCPs) wurden mit einer Reihe von Elektrophilen abgefangen, einschließlich Carbonsäurechloriden, Sulfonothioaten, Hydroxylaminobenzoaten, Tosylcyanid sowie Arylund Allylhalogeniden. Dadurchwurden hochfunktionalisierte BCP-Derivate erzeugt. Die ungewçhnlichh ohe Regioselektivitätd ieser Reaktionen wurde mittels DFT-Berechnungen rationalisiert. Ein Bioisoster des synthetischen Opioids Pethidin wurdem it Hilfe dieser Methodik in einem Schritt in 95 % Ausbeute hergestellt. Schema 1. A) Reaktion von [1.1.1]Propellan (1)mit Radikalen und Anionen. B) BCP-Analoga ausgewählter pharmazeutischer Verbindungen. Schema 2. Reaktionen von [1.1.1]Propellan (1)m it organometallischen Reagenzien.

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Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd‐Catalyzed Regiodivergent Couplings between Indazoles and Isoprene

Jiang

Zhang

et al. 2021

Angewandte Chemie

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Depending on the reactant property and reaction mechanism, one major regioisomer can be favored in areaction that involves multiple active sites.H erein, an orthogonal regulation of nucleophilic and electrophilic sites in the regiodivergent hydroamination of isoprene with indazoles is demonstrated. Under Pd-hydride catalysis,t he 1,2-or 4,3insertion pathway with respect to the electrophilic sites on isoprene could be controlled by the choice of ligands.Interms of the nucleophilic sites on indazoles,t he reaction occurs at either the N 1-o rN 2-position of indazoles is governed by the acid co-catalysts.P reliminary experimental studies have been performed to rationalizet he mechanism and regioselectivity. This study not only contributes ap ractical tool for selective functionalization of isoprene,b ut also provides ag uide to manipulate the regioselectivity for the N-functionalization of indazoles.

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Regioselektive Allyl‐Allyl‐Kreuzkupplungen ohne Übergangsmetallkatalysator

Cited by 8 publications

References 59 publications

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

Hoch regioselektive Addition von allylischen Zinkhalogeniden und verschiedenen Zinkenolaten an [1.1.1]Propellan

Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd‐Catalyzed Regiodivergent Couplings between Indazoles and Isoprene

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