Trimethylsilylmethyllithium
TMSMLi

Chemical formula (CH3)3SiCH2Li
Appearance colorless to yellow-brown solution

TMSMLi is a non-pyrophoric strong base. The advantages of this reagent are the low nucleophilicity toward pyridines in deprotonation reactions and the enhanced thermal stability (US Patent 7,129,360). It is also used with LiOCH2CH2NMe2 (LiDMAE) for α-lithiation and other novel selectivities for the lithiation of pyridines. (1) Tetrahedron 2006, 62, 6166. (2) Org. & Biomol. Chem. 2006, 4, 4331. (3) Chem. Commun. 2006, 2673.