Sodiation of Arenes and Heteroarenes in Continuous Flow.

The first sodiations of (hetero)arenes in continuous flow using NaDA (sodium diisopropylamide) in Me2 EtN 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.