Synthesis 2010(3): 395-397  
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

Fatemeh Jabbari*, Akbar Saednya
Faculty of Chemistry, University of Tabriz, Tabriz, Iran
Fax: +98(411)340191; e-Mail: f_jabary3055@yahoo.com;
Further Information

Publication History

Received 2 October 2009
Publication Date:
07 December 2009 (online)

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.