The Photostimulated S RN1 Process: Reaction of Haloarenes with Carbanions

For unactivated aromatic and heteroaromatic substrates, where a polar substitution is not favorable, nucleophilic substitution is feasible through processes that involve electron transfer (ET) steps. In these reactions, an aromatic compound bearing an adequate leaving group is substituted at the

ipso

position by a nucleophile in a unimolecular radical nucleophilic substitution mechanism (or S

1), which is a chain process that involves radicals and radical anions as intermediates.