Sodiation of Arenes and Heteroarenes in Continuous Flow

Abstract

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.