Green and convenient arene-catalized reductive lithiation of heterocyclic compounds

In the last decades reductive lithiation established itself as a particularly powerful procedure for the generation of functionalized organometals. In addition, the enormous role of this reaction in the reductive ring opening and functionalization of heterocycles has been reported. Accordingly, critical experiments were performed for the generation of lithium radical anions of several PAHs and a diene in both solvents, under both CA and SA protocols. Almost all of the above mentioned hydrocarbons rapidly generate radical anions with different fascinating visible colors at 0 °C. Based on this, influence of different electron shuttles and their efficiency in the reductive lithiation of N-phenylaziridine, phthalan will be disclosed. Moreover, we will report an interesting example of chemoselectivity concerning to the reductive lithiation of 4-chlorobenzyl methyl ether in a green solvent.