8.1.14.23 Hetaryllithium Compounds (Update 2025)

Abstract

This is an update to the previous Science of Synthesis chapter on aryl and hetaryllithium compounds (Section 8.1.14). This update is focused solely on hetaryllithium compounds and covers those advances in the preparation and the reactivity of lithiated hetarenes described in articles that were published between 2004 and 2023. Reviewed herein are direct deprotonation, halogen–lithium exchange, and directed metalation strategies to access a diverse range of lithiated nitrogen-, oxygen- or sulfur-based hetarenes. Selected classical strategies to prepare hetaryllithium compounds covered in the previous chapter are also included in this update, since novel applications and further transformations of these hetaryllithium compounds have been explored.