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- Title
Halogen-Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate.
- Authors
Qingqiang Tian; Suqin Shang; Huajun Wang; Guoqiang Shi; Zhiyao Li; Jianyong Yuan
- Abstract
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.
- Subjects
HALOGENS; BROMINE; QUENCHING (Chemistry); CHEMICAL reagents; CHELATION
- Publication
Molecules, 2017, Vol 22, Issue 11, p1952
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules22111952