Synthesis 2010(15): 2670-2678  
DOI: 10.1055/s-0029-1218845
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Preparation of Polyfunctional Organometallics via Directed ortho-Metalation

Stefan H. Wunderlich, Tomke Bresser, Cora Dunst, Gabriel Monzon, Paul Knochel*
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 22 April 2010
Publication Date:
29 June 2010 (online)

Abstract

Highly functionalized organometallics are efficiently prepared in larger quantities (up to 4 g) by directed ortho-metalation using the previously reported amide bases TMP2Mn˙2MgCl2˙4LiCl (TMP = 2,2,6,6-tetramethylpiperidyl), TMP2Fe˙2MgCl2˙4LiCl and TMP3La˙3MgCl2˙5LiCl. The resulting organometallics undergo various reactions with electrophiles like acid chlorides, alkyl iodides, or aldehydes and provide the corresponding products in good to excellent yields.