title: Preparation and Regioselective Magnesiation or Lithiation of Bis(trimethylsilyl)methyl-Substituted Heteroaryls for the Generation of Highly Functionalized Heterocycles.
abstract: A wide range of bis(trimethylsilyl)methyl (BTSM)- substituted heteroaryl derivatives has been prepared by using Kumada-Corriu or Negishi cross-coupling reactions. The regioselective lithiation or magnesiation of these building blocks bearing a bulky BTSM group by using magnesium or lithium 2,2,6,6-tetramethylpiperidide bases followed by quenching reactions with different electrophiles provides various functionalized N-, O-, or S-heterocycles. Furthermore, the BTSM group can then be converted into formyl, methyl, or styryl groups to give access to a variety of highly functionalized heteroaromatics.
authors: Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680.
authors: Thomas
authors: T
authors: Klatt
authors: Veronika
authors: V
authors: Werner
authors: Marina G
authors: MG
authors: Maximova
authors: Dorian
authors: D
authors: Didier
authors: Yitzhak
authors: Y
authors: Apeloig
authors: Paul
authors: P
authors: Knochel
keywords: heterocycles; magnesium; metalation; silyl reagents; synthetic methods