Directed Magnesiation of Haloaromatics Oxazolines using the Tetramethylpiperidylmagnesium Reagents TMPMgCl.LiCl

Directed Magnesiation of Haloaromatics Oxazolines using the Tetramethylpiperidylmagnesium Reagents TMPMgCl.LiCl

Batista; J.H.C.; Santos; F.M.; Silva; S.C.; Oliveira; A.R.M.; Clososki; G.C

Abstract:

The metallation of aromatics is a convenient approach to the functionalization of unsaturated scaffolds. Especially polyfunctional aryl halides are of high importance as agrochemicals, pharmaceuticals and building blocks. Recently, we have reported the preparation of highly reactive magnesium TMP amides such TMP2Mg.2LiCl and TMPMgCl.LiCl which proved able to magnesiate several aromatics under mild conditions. The aim of this work is to report the application of magnesium amides for the magnesiation of several haloaromatics oxazolines and subsequent reactions with electrophiles.

The metallation of aromatics is a convenient approach to the functionalization of unsaturated scaffolds. Especially polyfunctional aryl halides are of high importance as agrochemicals, pharmaceuticals and building blocks. Recently, we have reported the preparation of highly reactive magnesium TMP amides such TMP2Mg.2LiCl and TMPMgCl.LiCl which proved able to magnesiate several aromatics under mild conditions. The aim of this work is to report the application of magnesium amides for the magnesiation of several haloaromatics oxazolines and subsequent reactions with electrophiles.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20139152215

Referências bibliográficas

• [1] 1 a) N. Chatani, Directed Metallation, in: Topics in Organometallic Chemistry, Springer, Berlim, 2007. b) R.E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. 2007, 119, 3876.
• [2] 2 K.C. Nicolaou, T. Montagnon, Molecules that Changed the World: A Brief History of the Art and Science of Synthesis and its Impact on Society, Wiley-VCH, Weinheim, 2008.
• [3] 3 T. Kunz, P. Knochel, Angew. Chem. 2012, 124, 1994; Angew. Chem. Int. Ed. 2012, 51, 1958.

Como citar:

Batista, ; J.H.C., ; Santos, ; F.M., ; Silva, ; S.C., ; Oliveira, ; A.R.M., ; Clososki, ; G.C, ; "Directed Magnesiation of Haloaromatics Oxazolines using the Tetramethylpiperidylmagnesium Reagents TMPMgCl.LiCl", p-13-13. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20139152215