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Directed Functionalization of Halophenyl‐2‐oxazolines with TMPMgCl·LiCl

2014; Wiley; Volume: 2015; Issue: 5 Linguagem: Inglês

10.1002/ejoc.201403255

1434-193X

João Henrique Carvalho Batista, Fernanda M. dos Santos, Leandro A. Bozzini, Ricardo Vessecchi, Alfredo R. M. Oliveira, Giuliano C. Clososki,

Synthesis of heterocyclic compounds

Abstract A variety of difunctionalized aryl‐2‐oxazolines were prepared from the reaction of halophenyl‐2‐oxazolines and TMPMgCl · LiCl to give an organomagnesium reagent, which was then treated with various electrophiles. The metalation step takes place under mild conditions, and this process allows for the isolation of the desired products in good yields. No isomeric or other benzyne‐derived products were detected. The influence of the halogen substituents on the acidity of the aromatic hydrogen atoms was evaluated by using density functional theory (DFT) calculations.