Preparation of Diorganomagnesium Reagents by Halogen–Lithium Exchange of Functionalized Heteroaryl Halides and Subsequent in situ Trapping with MgCl2·LiCl in Continuous Flow

Rodolfo Hideki Vicente Nishimura; Niels Weidmann; Paul Knochel

doi:10.1055/s-0040-1707167

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(20): 3036-3046
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

Rodolfo Hideki Vicente Nishimura

^aColegiado de Ciências Farmacêuticas, Universidade Federal do Vale do São Francisco, Avenue José de Sá Maniçoba, Petrolina, 56304-205 Petrolina, Brazil

,

Niels Weidmann

^bLudwig-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, 81377 München, Germany eMail: Paul.knochel@cup.uni-muenchen.de

,

Paul Knochel ∗

^bLudwig-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, 81377 München, Germany eMail: Paul.knochel@cup.uni-muenchen.de

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Abstract

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^‡ 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 exchange

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