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Synlett 2001; 2001(4): 0477-0480
DOI: 10.1055/s-2001-12323
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Preparation of Functionalized Magnesiated Aniline Derivatives

Greta Varchi* , Anne Eeg Jensen, Wolfgang Dohle, Alfredo Ricci, Gérard Cahiez, Paul Knochel
  • *Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany; Fax + 49-89-21 80 76 80; E-mail: knoch@cup.uni-muenchen.de
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Publication Date:
31 December 2001 (online)

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Functionalized magnesiated aniline derivatives were readily prepared by using a bromine- or iodine-magnesium exchange. Formamidine or benzimine were found to be excellent protecting groups of the amino function for the generation of functionalized aminated Grignard reagents. These organomagnesium reagents react with various electrophiles such as aldehydes, iodoenones and allylic halides in excellent yields. After transmetallation with ZnBr2, Pd(0)-catalyzed cross-coupling with aryl iodides can be readily performed.

magnesium - heterocycles - bromine-magnesium exchange - cross-coupling reactions

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