A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones

α-Halomethyllithium carbenoids are useful homologating reagents which - reacting under proper reaction conditions as carbanions - enable the installation via nucleophilic addition of a reactive halomethyl fragment onto a preformed carbon-heteroatom bond. The pronounced thermolability represented - since seminal studies by Köbrich - the Achilles' heel of these reagents: the use of Barbier-type methodologies (i.e., the electrophile should be present in the reaction mixture prior to the formation of the carbenoid) was pivotal in order to suppress decomposition through α-elimination processes. Nowadays, the use of low temperatures (-78 °C) guarantees reliable procedures and, significantly, the employment of microreactor technologies allows external trapping to be performed even at higher temperatures as reported by Luisi. We will discuss the α-halomethyllithium-mediated homologations of a series of carbon electrophiles such as carbonyl compounds, imines, esters, Weinreb amides, and isocyanates.

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Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

Monticelli

Castoldi

Murgia

et al. 2016

Monatsh Chem

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Since the introduction of 2-methyltetrahydrofuran as an useful alternative to the classical tetrahydrofuran, there has been a continuous interest in the synthetic community operating at academic and industrial towards it. In particular, the much higher stability that basic organometallic reagents display in 2-methyltetrahydrofuran makes it suitable for processes involving such sensitive species including asymmetric transformations. The easy formation of an azeotropic mixture with water, the substantial immiscibility with water, and the fact it derives from natural sources (corncobs or bagasse), allow to consider it in agreement with the Anastas’ Geen Chemistry principles. In this minireview, selected examples of its employment in organometallic transformations ranging from carbanions to radical and transition metal-catalyzed processes are provided.Graphical abstract

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A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones

Cited by 11 publications

References 44 publications

ChemInform Abstract: A Straightforward and General Access to α‐Phthalimido‐α′‐substituted Propan‐2‐ones.

ChemInform Abstract: A Straightforward and General Access to α‐Phthalimido‐α′‐substituted Propan‐2‐ones.

Lithium Halomethylcarbenoids: Preparation and Use in the Homologation of Carbon Electrophiles

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

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