Alkyl halides with lithium

The reaction of an alkyl halide with lithium is an oxidation-reduction reac tion Group I metals are powerful reducing agents... 

Many other kinds of organometallic compounds can be prepared in a manner similar to that of Grignard reagents. For instance, alkyllithium reagents, RLi, can be prepared by the reaction of an alkyl halide with lithium metal. Alkyllithiums are both nucleophiles and strong bases, and their chemistry is similar in many respects to that of alkylmagnesium halides. 

Alkyllithium can be easily prepared by reacting an alkyl halide with lithium metal in an ether solvent. 

Organolithium reagents These reagents are prepared by the reaction of alkyl halides with lithium metals in an ether solvent. Unlike Grignard reagents, organolithiums can also be prepared using a variety of hydrocarbon solvents e.g. hexane, and pentane. 

Ashby, E. C. Park, W. S. Goel, A. B. Su, W.-Y. Single-electron transfer in reactions of alkyl halides with lithium thiolates./. Org. Chem. 1985, 50, 5184-5193. 

Longer-chain alkyl halides may not be commercially available, but they are readily made in one step from the corresponding alcohols (Larock, 1999), as are tosylates and mesylates. Similarly, longer-chain terminal alkynes are not commercially available, but can be readily made by reaction of alkyl halides with lithium acetylide-ethylene diamine complex in dry... 

Table 4 Reduction of Alkyl Halides with Lithium Triethylborohydride in THF ...

Simple, unfunctionalized organolithium compounds are usually prepared by reductive lithiation of alkyl halides with lithium metal at ambient temperature or above [26]. Reductive lithiation is fastest for alkyllithium compounds (the more substituted the better) and slowest for aryllithium compounds. The order of reactivity follows logically from the relative stabilities of the intermediate radicals, whose formation is the rate-determining step of the sequence. 

Hindered t-alkyl halides with lithium triethylborohydride in the presence of chromous chloride furnish highly crowded coupled products in good yield (equation 111) . Alkanes obtained by hydroalumination of alkenes with LAH in the presence of titanium tetrachloride can be dimerized in the presence of cupric acetate to furnish alkanes (equation 112) ... 

Substitution reaction of alkyl halide with lithium dialkyl cuprates (9.8)... 

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