Optimization of Organolithium Reactions

Over the last several decades, research directed at optimization of reactions involving organolithium reagents has led to the recognition that a variety of experimental parameters may affect the outcome and viability of such reactions. Investigation of the factors that influence organolithium-mediated reactions on a large scale is a requirement for development of a feasible and practical process. This contribution critically reviews selected examples, taken from the literature, in which adjustment of the reaction medium, order of addition, temperature, the presence of additives, and judicious choice of base, substrate and/or electrophile resulted in optimization of processes involving organolithium reactions.