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Synthesis 2020; 52(20): 3036-3046
DOI: 10.1055/s-0040-1707167
DOI: 10.1055/s-0040-1707167
paper
Preparation of Diorganomagnesium Reagents by Halogen–Lithium Exchange of Functionalized Heteroaryl Halides and Subsequent in situ Trapping with MgCl2·LiCl in Continuous Flow
Funding Information: Studienstiftung des Deutschen Volkes, (Grant / Award Number: ) Fundação de Amparo à Pesquisa do Estado de São Paulo, (Grant / Award Number: '2018/08856-5')R. H. V. Nishimura thanks Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, Grant number: 2018/08856-5) for financial support. N. Weidmann thanks the German Academic Scholarship Foundation for a fellowship. We thank the DFG and LMU for financial support. We further thank BASF (Ludwigshafen) and Albemarle (Frankfurt) for the generous gift of chemicals, and Vapourtec and Uniqsis for technical support.
Further Information
Publication History
Received: 28 May 2020
Accepted after revision: 30 May 2020
Publication Date:
29 June 2020 (online)
‡ These authors contributed equally.
In memory of Prof. Dr. Rolf Huisgen
Abstract
A halogen–lithium exchange in the presence of MgCl2·LiCl on a broad range of heterocyclic scaffolds using a commercial flow set-up with nBuLi as exchange reagent is reported. The resulting diheteroarylmagnesium species were subsequently trapped with various electrophiles, such as ketones, aldehydes, allylic bromides, or disulfides affording functionalized heterocycles. A scale-up was performed by simply increasing the run-time without further optimizations.
Key words
heterocycles - flow chemistry - organomagnesium reagents - transmetalation - halogen–lithium exchangeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707167.
- Supporting Information
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General advances in flow chemistry: