0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
4.4.11 Silyllithium and Related Silyl Alkali Metal Reagents

DOI: 10.1055/sos-SD-104-00454

Kleeberg, C.Science of Synthesis Knowledge Updates, (20171177.

General Introduction

Silyllithium derivatives, and to a lesser extent also the related silyl compounds of the heavier alkali metals, are widely used as reagents in organic as well as inorganic transformations. The most common application is the nucleophilic introduction of silyl groups into organic molecules or (organometallic) metal complexes. Hence, formally similar transformations are conducted with these reagents to those that are widely established for organolithium reagents. Typical transformations employing silyllithium reagents in synthetic organic chemistry are nucleophilic substitution reactions with organohalides and 1,2-addition to carbonyl or carboxy groups, as well as their vinylogous counterparts, but other reactions have also been reported (see, for example, Sections,,,, and[‌1‌‌6‌] In the field of inorganic chemistry, transmetalation, salt metathesis, and ligand addition reactions are typical applications of silyllithium derivatives and their heavier analogues. An example is the synthesis of silyl complexes of main-group as well as transition-metal complexes (e.g., see Sections and[‌1‌,‌3‌,‌4‌]

Meeeeee eee eeeeeeeee eeeeeeeeeee ee eeeee eeeeee eeeee eeeeeeee, eeee eeeeeeeeeee eeeeeeeeeeee eeeeeeee, eeee e eeeeeeeeee eeeee eeeeee ee eeeeee eeeee eeeeee eeeeee ee eeeeeeeeeeee eeee eee, eeeeeeee eeeeeeeee eeeeeeeee ee eeee-eeeeeee, eeeeeeeeeeeeee ee eeeeee eee eeeeeeeeeeeeeeee eeeeeeee eeeeeeeeeeee eeeeeeeeeee eeee eeee eeeeeeee.[‌8‌,‌8‌,‌8‌‌88‌] Meeeeeee ee eeeeee, eeeeeeeeee eeee eeeeeeeeeeee eeeeeeee eeeeeee eeeeeeee(eeeeee)eeeeeeeeeeee (Me8MeMeMe, 8), eeeeeeeeeeeeeeeeeeeee (Me8MeMe), eee (eee-eeee-eeeeeeeeee)eeeeeee ­[(e-Me)8MeMe (8, M = Me)] ee eeee ee eeeeeeeeeeeeeeeeeeeee (Me8MeMe, 8) eee eeee(eeeeeeeeeeeeee)eeeeeeeeeeee [(MMM)8MeMe].

Meeee eee eeeeeeeee ee eeee eeeeeeeeeeee eeeeeeee eee eeee eeeeeeeee, eeeeeeeeeeee eeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee ee eeee. Meeee, eeeeeeeeeeee eeeeeeeee ee eeeeeee eee, eeeee, eee eeeeee ee eeeeeeeeeeee eeeeeee ee eeeeeeeee eeee eee eeeeeeeeeeeee ee eee eeeeeeee. Meeeeeeeeee, eeeeeee eeeee ee eeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee. Me eee eeeeeeeee eeeeee eeeeeeeee eeeeee, eeeeeee eee eeeee eeee eeeeeee ee eeeeeeeeee eeeee eeeeeeeeee. Meee, eeeeeeee, ee eeeeeeeeeeee, e.e. 8,8-eeeeeeeeeeeee ee eeeee eeeeeee, ee eeeee ee eee eeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeeeee eeee eee eeeeeeeeeeee eee, eeeee eeeeeeeeee, eee eeeeeeee eeee (eeeee, eee-eeeee eeeee eeeeeee, e.e. eeeeeeeeee ee eeeeeeee) ee eeeeeeeeee. Meee eee eeeeeeeeee eeeeeee eee eee, eee eeeeee ee eeeeeeeeeeee eeeeeee eee ee eeeeeee.[‌88‌‌88‌] Meeeeee, eeeeeeeeeee eeee eee eeeee eeee ee eeeeeeeee eeeee eeeeeeeeee eee eeee eeeeeeee ee eeeeeee.[‌88‌] Meeeeeee, eeeeeeee eeeeeeeeeeeee ee eee eeeeee eeeeeeeee eeeeee ee eee eeeeeeee ee eeeeeeeeeeeee/eeeeeeeeeeeee eeeeeeee eeee eeee eeeeeeeee,[‌88‌] eee ee eee eeee ee eeeeeeeeeee ee eeeeeeeee eeeeeeee eeee ee eeeeeee eeeee, eeeeeeeeeeeee eeeeeeeee, ee eeeee eeeeeeee (eee eeeee).[‌88‌]

Meeeee eeee eeeeeee, eeeeeeee eeeeeee eee eee eeeeeeeeee ee (eeeeee) eeeeeeeeeeee eeeeeeee, eee eeee eeeee eeeeeee eeeeeee eeeeee eeeee eeeeeeeee, eee eeeeeeeee. Mee eeeeeee eeee ee eeeeee eeee eee eeeeee eeeee eeeee ee eeeeeeee ee eeeeeeee ee e eeeeeee–eeeeeee eeee. Mee eeeeeeeee eeeeeee eee eeeeeeeeeee ee eee eeeeeeee eeeeeee eee eee eeee ee eeeeeeee eeeeeeee. Meee eeeeee eeeeeeee eeeeeee, eeee ee Me—M, Me—Me, Me—Me, ee Me—M eeee eeeeeeee eee eee eeeeeeeee ee eeeeee.[‌8‌,‌88‌‌88‌]

M eeeeee ee eeeeeeeeeeeee eeeeeee eeeeeeeeee eee eeee eee eeeeeeeee eee eeee eee eeeeeeeeee, eeeeeeeeee, eeeeeeeeeeeee eeeeeeeeee, eee eeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee eee eeeeeee eeeeeeee eeee eeee eeeeeeeee eee eee eeeeeeeeeee eee eeeeeee eeeeeee.[‌8‌‌8‌,‌88‌,‌88‌]