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Synthesis 2011(11): 1751-1758
DOI: 10.1055/s-0030-1260035
DOI: 10.1055/s-0030-1260035
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Regio- and Chemoselective Synthesis of Fully Substituted Furans
Further Information
Received
22 January 2011
Publication Date:
10 May 2011 (online)
Publication History
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