Directed Magnesiation of Haloaromatic Oxazolines using the mixed lithium/magnesium base TMPMgCl.LiCl

Directed Magnesiation of Haloaromatic Oxazolines using the mixed lithium/magnesium base 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 scaffolds1. Polyfunctional ary halides are of high importance as agrochemicals, pharmaceuticals and building blocks. Recently, mixed lithium/magnesium amides such as TMPMgCl.LiCl and TMP2Mg.2LiCl have proven to be interesting bases for functionalization of arenes under mild conditions. In this work we wish to report the use 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 scaffolds1. Polyfunctional ary halides are of high importance as agrochemicals, pharmaceuticals and building blocks. Recently, mixed lithium/magnesium amides such as TMPMgCl.LiCl and TMP2Mg.2LiCl have proven to be interesting bases for functionalization of arenes under mild conditions. In this work we wish to report the use 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_201391521546

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 Haloaromatic Oxazolines using the mixed lithium/magnesium base TMPMgCl.LiCl", p-98-98. 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_201391521546