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Synthesis 2011(11): 1751-1758  
DOI: 10.1055/s-0030-1260035
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regio- and Chemoselective Synthesis of Fully Substituted Furans

Fabian M. Piller, Paul Knochel*
Department Chemie, , Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 22 January 2011
Publication Date:
10 May 2011 (online)

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Abstract

Highly functionalized furyl-, indolyl-, and pyrrolylmagnesium reagents are efficiently prepared by direct C-H activation by using regio- and chemoselective magnesium amide bases, such as (tetramethylpiperidyl)magnesium chloride-lithium chloride (TMPMgCl˙LiCl) or bis(tetramethylpiperidyl)magnesium-bis(lithium chloride) (TMP2Mg˙2LiCl), tolerated by a range of sensitive functional groups. These organometallic reagents readily react with various electrophiles, leading to polyfunctional heterocycles. Furthermore, the full functionalization of the sensitive furan scaffold can be achieved.

Key words

directed metalation - organometallic reagents - metal amides - magnesium - furan

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Determined by GC analysis of an iodolyzed reaction aliquot