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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 4.4.21.4, 4.4.28.8.1, 4.4.28.8.4, 4.4.36.6, and 4.4.40.25).[‌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 4.4.7.1.1 and 4.4.7.1.2).[‌1‌,‌3‌,‌4‌]

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