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Synthesis 2019; 51(07): 1649-1654
DOI: 10.1055/s-0037-1611938
DOI: 10.1055/s-0037-1611938
paper
Selective ortho-Metalation of a Fluoroarene with Knochel–Hauser Base and Reactions with Various Electrophiles
Further Information
Publication History
Received: 02 October 2018
Accepted after revision: 13 November 2018
Publication Date:
08 January 2019 (online)
Abstract
Selective ortho-metalation of 1-bromo-2-(1,1-difluoroethyl)-4-fluorobenzene was achieved with the Knochel–Hauser base (TMPMgCl·LiCl) in position 5 of the aromatic ring. The magnesiated intermediate was reacted with a variety of electrophiles to obtain the products in good yields. The work was successfully extended to a Negishi coupling, after transmetalation with ZnCl2 and Pd-catalyzed reaction with 4-iodotoluene.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611938.
- Supporting Information
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