Bis 2-pyridyldimethylsilyl methyl lithium

Form Supplied in prepared in situ and used directly. 

Preparative Methods deprotonation of bis(2-pyridyldimethyl-silyl)methane by n-butyllithium in dry Et20 at —78 °C under argon. 

Introduction. The Peterson-type olefination reaction has emerged as an extremely useful method for the preparation of alkenes from carbonyl compounds. Synthetically useful vinylsilanes can be prepared by using the Peterson-type olefination reaction of bis(silyl)methylmetal with carbonyl compounds. Among the various reported bis(silyl)methyhnetals, [bis(2-pyri-dyldimethylsilyl)methyl]lithium is an extremely efficient reagent for the stereoselective preparation of vinylsilane.  

The S3nthesis of the starting material bis(2-p)ridyldimethylsilyl) methane can be easily accomplished in one-pot by the deprotonation of 2-pyridyltrimethylsilane with t-BuLi followed by reaction with 2-pyridyldimethylsilane (eq 1). The subsequent generation of [bis(2-pyridyldimethylsilyl)methyl]lithium is easily accomplished by the deprotonation ofbis(2-p)ridyldimethylsilyl) methane with -butyUithium in dry diethyl ether (eq 2).  

A list of General Abbreviations appears on the front Endpapers 

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Table 1 Reactions of [bis(2-pyridyldimethylsilyl)methyl]lithium with carbonyl compounds ...

Reaction of [bis(2-pyridyldimethylsilyl)methyl]lithium with Carbonyl Compounds. The Peterson-t)fpe reaction of [bis(2-pyridyldimethylsilyl)methyl]lithium with primary, secondary, and tertiary aliphatic and aromatic aldehydes produces the corresponding 2-pyridyl-suhstituted vinylsilanes in essentially quantitative yields (entries 1-7, Table 1, eq 3). The reaction is also applicable to sterically hindered aldehydes (entries 3 and 6) and di-aldehyde (entry 7). The reactions with ketones give disubstituted vinylsilanes with somewhat lower yields (entries 8-10). The reaction can be applied to the stereoselective synthesis of dienylsilanes as well (entries 11-13). In all cases, the reaction occurs in a complete stereoselective fashion (>99% E). 

PyrMe2Si, 2-PyrMe2Si HCLi [Bis(2-pyridyldimethylsilyl)methyl]lithium 356062-49-2 54... 

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