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Molecules 2017, 22(11), 1952; doi:10.3390/molecules22111952

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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Received: 18 October 2017 / Revised: 2 November 2017 / Accepted: 9 November 2017 / Published: 11 November 2017
(This article belongs to the Section Organometallic Chemistry)
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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. View Full-Text
Keywords: acidic proton; non-cryogenic; arene; bromine–metal exchange acidic proton; non-cryogenic; arene; bromine–metal exchange
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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