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Weidmann, Niels; Ketels, Marthe; Knochel, Paul (2018): Sodiation of Arenes and Heteroarenes in Continuous Flow. In: Angewandte Chemie-International Edition, Vol. 57, No. 33: pp. 10748-10751
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The first sodiations of (hetero)arenes in continuous flow using NaDA (sodium diisopropylamide) in Me2EtN are reported. This flow procedure enables sodiation of functionalized arenes and heteroarenes that decompose under batch-sodiation conditions. The resulting sodiated (hetero)arenes react instantly with various electrophiles, such as ketones, aldehydes, isocyanates, alkyl bromides, and disulfides, affording polyfunctionalized (hetero)arenes in high yields. Scale-up is possible without further optimization.