Organolithium compounds have long been indispensable and versatile tools in synthesis. Their vast scope of reactivity enables them to be utilized as, for example, brilliant bases, nucleophiles, and reducing agents in organic chemistry. They are also found traversing essentially the whole periodic table as ligand transfer agents to metals in main group, transition metal and lanthanide/actinide chemistry. For this reason, organolithium and related lithium amide compounds have found a wealth of applications in industry, for example, in the manufacture of fine chemicals, pharmaceuticals and polymers. While lithium has punched above its weight in this important area of polar organometallic chemistry, in contrast the heavier alkali metals have not commanded anything like the same extensive usage, though certain organosodium and organopotassium compounds are well known for selected specialized roles. Today, rubidium and cesium organometallic chemistry still requires significant fundamental development and in general most chemists would perceive them as exotic rarities. This presentation will focus on our recent progress in this development and draw direct comparisons with related chemistry of the lighter alkali metal congeners. It discusses successful catalytic transfer hydrogenation reactions of alkenes using heterobimetallic alkali metal magnesium amide complexes and of imines using homometallic alkali metal complexes. Interestingly, under the conditions studied where the hydrogen source is 1,4-cyclohexadiene, the alkali metal heavyweights substantially outperform their lighter congeners. Results from DFT calculations carried out to shed light on the reactivity trends observed in these experiments will also be reported. Alkali metals also play a pivotal part in the synthesis and stabilization of low valent aluminum chemistry. Our synthetic and structural contributions to this emerging area of main group chemistry will also be discussed.

Alkali metal heavyweights: Potential big hitters in homogeneous catalysis

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