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Synthesis 2010(3): 395-397
DOI: 10.1055/s-0029-1218593
DOI: 10.1055/s-0029-1218593
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Novel One-Pot Synthesis of Different Derivatives of Tetraarylterephthalaldehyde via a Multiple Aryne Sequence
Weitere Informationen
Received
2 October 2009
Publikationsdatum:
07. Dezember 2009 (online)
Publikationsverlauf
Publikationsdatum:
07. Dezember 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/201003/lookinside/thumbnails/10.1055-s-0029-1218593-1.jpg)
Abstract
The synthesis of a novel series of tetraarylterephthalaldehyde derivatives in an one-pot reaction is described. In this methodology 1,2,4,5-tetrachloro-3,6-diiodobenzene is treated with various aryl Grignard reagents (excess) in tetrahydrofuran to give tetraarylbenzene-1,4-diylbis(magnesium bromides). After reaction of this product with ethyl formate and aqueous quench, tetraarylterephthalaldehydes are isolated in 33-80% yields. A mechanism involving organometallic aryne intermediates is proposed.
Key words
tetraarylterephthalaldehyde - 1,2,4,5-tetrachloro-3,6-diiodobenzene - aryl Grignard reagents - tetraarylbenzene-1,4-diylbis(magnesium bromide) - ethyl formate
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