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Selective ortho -Metalation of a Fluoroarene with Knochel-Hauser Base and Reactions with Various Electrophiles

Baenziger, Markus and Eswaran, Sumesh and Kanasithan, Gopu and Jiang, Yifan (2019) Selective ortho -Metalation of a Fluoroarene with Knochel-Hauser Base and Reactions with Various Electrophiles. Synthesis (Germany), 51 (7). pp. 1649-1654. ISSN 1437210X

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 ZnCl 2 and Pd-catalyzed reaction with 4-iodotoluene.

Item Type: Article
Keywords: fluoroaromatic Knochel-Hauser base Negishi coupling ortho -metalation TMPMgCl·LiCl
Date Deposited: 28 May 2019 00:45
Last Modified: 28 May 2019 00:45
URI: https://oak.novartis.com/id/eprint/37850

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