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首页> 美国卫生研究院文献>Chemical Science >Water opens the door to organolithiums and Grignard reagents: exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans
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Water opens the door to organolithiums and Grignard reagents: exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans

机译：水打开了有机锂和格氏试剂的大门：探索和比较非常规反应介质中高极性有机金属化合物对四氢呋喃合成的反应性

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摘要

It has always been a firm conviction of the scientific community that the employment of both anhydrous conditions and water-free reaction media is required for the successful handling of organometallic compounds with highly polarised metal–carbon bonds. Herein, we describe how, under heterogeneous conditions, Grignard and organolithium reagents can smoothly undergo nucleophilic additions to γ-chloroketones, on the way to 2,2-disubstituted tetrahydrofurans, “on water”, competitively with protonolysis, under batch conditions, at room temperature and under air. The reactivity of the above organometallic reagents has also been investigated in conventional anhydrous organic solvents and in bio-based eutectic and low melting mixtures for comparison. The scope and limitations of this kind of reaction are discussed.
机译：科学界一直坚信，要成功处理具有高度极化的金属-碳键的有机金属化合物，必须同时使用无水条件和无水反应介质。本文中，我们描述了在异质条件下，格氏试剂和有机锂试剂如何在“水上”与质子分解，分批条件下，在室温下“顺水”竞争地顺利地向γ-氯酮进行亲核加成反应。温度和空气中。还比较了上述有机金属试剂在常规无水有机溶剂中以及在生物基共晶和低熔点混合物中的反应性，以进行比较。讨论了这种反应的范围和局限性。

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