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

Pharmacy College, Chongqing Medical University, Chongqing 400016, China
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Molecules 2017, 22(11), 1952; https://doi.org/10.3390/molecules22111952
Received: 18 October 2017 / Revised: 2 November 2017 / Accepted: 9 November 2017 / Published: 11 November 2017
(This article belongs to the Section Organometallic Chemistry)
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. View Full-Text
Keywords: acidic proton; non-cryogenic; arene; bromine–metal exchange acidic proton; non-cryogenic; arene; bromine–metal exchange
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MDPI and ACS Style

Tian, Q.; Shang, S.; Wang, H.; Shi, G.; Li, Z.; Yuan, J. Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate. Molecules 2017, 22, 1952.

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