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Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate
oleh: Qingqiang Tian, Suqin Shang, Huajun Wang, Guoqiang Shi, Zhiyao Li, Jianyong Yuan
Format: | Article |
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Diterbitkan: | MDPI AG 2017-11-01 |
Deskripsi
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 of i-PrMgCl and n-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.