Deprotonative Generation and Trapping of Haloaryllithium in a Batch Reactor
Yuxuan Feng, Taro Yukioka, Mei Matsuyama, Atsunori Mori, Kentaro Okano
Abstract
A method for the regioselective functionalization of haloarenes through deprotonative lithiation is disclosed. The generated haloaryllithiums were trapped in a batch reactor with a zinc chloride diamine complex to provide organozinc species without aryne formation, which reacted with electrophiles to afford the corresponding products in 38-98% yields. This method was applied to the five-step total synthesis of carbazomycin A on a gram scale in 33% overall yield.
Topics & Concepts
ChemistryRegioselectivityElectrophileYield (engineering)ZincCombinatorial chemistryTrappingChlorideSurface modificationOrganic chemistryCatalysisPhysical chemistryMetallurgyEcologyBiologyMaterials scienceCoordination Chemistry and OrganometallicsAsymmetric Synthesis and CatalysisCatalytic Cross-Coupling Reactions