Deprotonative Generation and Trapping of Haloaryllithium in a Batch Reactor

Org Lett. 2023 May 5;25(17):3013-3017. doi: 10.1021/acs.orglett.3c00800. Epub 2023 Apr 21.

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.