Alkyllithium reagents are important tools for the synthetic chemist. These reagents are commonly used as initiators for living polymerizations, as reagents for metalation of aryl halides, as nucleophiles for 1,2 additions to electrophiles, and as strong bases for the formation of hindered bases. The highly reactive nature of these reagents requires them to be sold in non-reactive but flammable alkane solvents such as pentane or hexane, making them very hazardous for laboratory use. Here, we report the use of liquid poly(α-olefin) (PAO) solvents with modest molecular weights as solvents for alkyllithium reagents. These oligomeric solvents are similar to traditional alkane solvents in terms of reactivity, but have very low flammability, making them much safer as solvents for alkyllithium reagents. Organolithium reagents in PAO do not readily ignite when exposed to air, and remain viable in air for &gt;1 h. Reactions using alkylithium reagents in PAO solvents are similar to reactions using low molecular weight alkane solvents. The PAO solvent may be removed from reaction products by extraction or chromatography.

Safer solvents for alkyllithium reagents

2019 Spring National Meeting

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