TMPZnCl.LiCl: a new active selective base for the directed zincation of sensitive aromatics and heteroaromatics

Org Lett. 2009 Apr 16;11(8):1837-40. doi: 10.1021/ol900342a.

Abstract

A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF via direct zincation using TMPZnCl.LiCl, a new exceptionally mild and efficient base. Activated arenes and heteroarenes are metalated at room temperature. Remarkably, sensitive functions such as an aldehyde as well as a nitro group are tolerated, expanding significantly the scope of directed metalations.