Abstract
Organolithium chemistry is broadly integrated and widely applied in studies that bridge inorganic, physical, organic, and theoretical chemistry.1 Reactions with organolithium species as reagents, reactants, or intermediates are so well established that organolithiums are the most widely used organometallics in contemporary organic chemistry. Deprotonative lithiations are commonly used to generate enolates, ylides, and dipole-stabilized, localized sp2 or sp or delocalized carbanions as reactive intermediates for diverse applications.2 A sequence in which a proton on a tetrahedral carbon is replaced by a substituent begins with removal of a proton from 1 to give the formally sp3 organolithium 2. Reaction of 2 with an electrophile subsequently provides 3.
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