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Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate

Qingqiang Tian,Suqin Shang,Huajun Wang,Guoqiang Shi,Zhiyao Li,Jianyong Yuan

A selective and practical bromine–metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination ofi-PrMgCl andn-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen–lithium exchange, but also offered a highly selective method for performing bromo–metal exchange on dibrominated arene compounds through chelation effect.Keywords:acidic proton;non-cryogenic;arene;bromine–metal exchange