Deprotonative Generation and Trapping of Haloaryllithium in a Batch Reactor.

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.