Zinc Chloro 2,2,6,6-Tetramethylpiperidide Lithium Chloride Complex, typ. 17 % solution in THF (typ. 0.7 M)
Selective deprotonation of arenes and heteroarenes.
Arenes and heteroarenes are typically deprotonated by a directed lithiation using organolithium compounds or organolithiumamides (e.g. LDA). The high reactivity and nucleophilicity of these reagents often result in unwanted side reactions and preludes the presence of sensitive functional groups like esters or ketones. Additionally, such deprotonation reactions often require low temperatures leading to higher production costs on larger scale.
Due to their low kinetic basicity zinc-amides tolerate a lot of functional groups.