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DOI: 10.1055/s-0029-1217129
A Convenient Two-Step Synthesis of 2-Arylbenzofurans
Publication History
Publication Date:
20 November 2009 (online)

Abstract
A novel and convenient two-step synthesis of 2-arylbenzofurans is described which proceeds via a selective cross-pinacol-type coupling between a salicylaldehyde and an aromatic aldehyde, followed by an acid-promoted cyclization. One advantage of this method is that separation of the three possible pinacol products that can form during the cross-coupling is not necessary. This method is also applied to the synthesis of the 2-arylbenzofuran-containing natural product, homoegonol.
Key words
pinacols - pinacol-type coupling - cross-coupling - benzofurans - 2-arylbenzofurans
- 1a
Friedrichsen W. In Comprehensive Heterocyclic Chemistry II Vol. 2:Katritzky AR.Rees CW.Scriven EFV. Pergamon Press; Oxford: 1996. p.259Reference Ris Wihthout Link - 1b
Donnelly DMX.Meegan MJ. In Comprehensive Heterocyclic Chemistry Vol. 4:Katritzky AR.Rees CW. Pergamon Press; London: 1984. p.531Reference Ris Wihthout Link - 1c
Cagniant P.Cagniant D. In Advances in Heterocyclic Chemistry Vol. 18:Katritzky AR.Boulton AJ. Academic Press; New York: 1975. p.337Reference Ris Wihthout Link - 1d
Hou X.-L.Yang Z.Yeung K.-S.Wong HNC. Prog. Heterocycl. Chem. 2005, 17: 142Reference Ris Wihthout Link - 1e
Hou X.-L.Yang Z.Wong HNC. Prog. Heterocycl. Chem. 2003, 15: 167Reference Ris Wihthout Link - 1f
McCallion GD. Curr. Org. Chem. 1999, 3: 67Reference Ris Wihthout Link - For selected recent references, see:
- 2a
Csekei M.Novak Z.Kotschy A. Tetrahedron 2008, 64: 8992Reference Ris Wihthout Link - 2b
Takashi O.Daisuke N.Rie T.Akimori W. Org. Lett. 2008, 10: 4967Reference Ris Wihthout Link - 2c
Grigg R.Sridharan V.Sykes DA. Tetrahedron 2008, 64: 8952Reference Ris Wihthout Link - 2d
Chen P.Wang J.Liu K.Li C. J. Org. Chem. 2008, 73: 339Reference Ris Wihthout Link - 2e
Roberta B.Sandro C.Ilse DS.Giancarlo F. Synthesis 2007, 873Reference Ris Wihthout Link - 2f
Russo O.Messaoudi S.Hamze A.Olivi N.Peyrat J.-F.Brion J.-D.Sicsic S.Isabelle B.-B.Alami M. Tetrahedron 2007, 63: 10671Reference Ris Wihthout Link - 2g
Li J.-H.Li J.-L.Wang D.-P.Pi S.-F.Xie Y.-X.Zhang M.-B.Hu X.-C. J. Org. Chem. 2007, 72: 2053Reference Ris Wihthout Link - 3a
Ackermann L.Kaspar LT. J. Org. Chem. 2007, 72: 6149Reference Ris Wihthout Link - 3b
Willis MC.Taylor D.Gillmore AT. Tetrahedron 2006, 62: 11513Reference Ris Wihthout Link - 3c
Carril M.SanMartin R.Tellitu I.Dominguez E. Org. Lett. 2006, 8: 1467Reference Ris Wihthout Link - 3d
Fang Y.Li C. J. Org. Chem. 2006, 71: 6427Reference Ris Wihthout Link - 3e
Chen C.-Y.Dormer PG. J. Org. Chem. 2005, 70: 6964Reference Ris Wihthout Link - 3f
Martinez A.Fernandez M.Estevez JC.Estevez RJ.Castedo L. Tetrahedron 2005, 61: 1353Reference Ris Wihthout Link - 3g
Willis MC.Taylor D.Gillmore AT. Org. Lett. 2004, 6: 4755Reference Ris Wihthout Link - 4a
Franck P.Hostyn S.Beata DH.Agnes PB.Monsieurs K.Matyus P.Maes BUW. Tetrahedron 2008, 64: 6030Reference Ris Wihthout Link - 4b
Ebisawa M.Ueno M.Oshima Y.Kondo Y. Tetrahedron Lett. 2007, 48: 8918Reference Ris Wihthout Link - 4c
Prado S.Toum V.Brigitte SJ.Michel S.Koch M.Cole ST.Tillequin F.Janin YL. Synthesis 2007, 1566Reference Ris Wihthout Link - For I2-mediated cyclizations, see:
- 5a
Pan C.-F.Yu J.Zhou Y.-Q.Wang Z.-Y.Zhou M.-M. Synlett 2006, 1657Reference Ris Wihthout Link - For the cyclization using DDQ, see:
- 5b
Takeshi K.Koji I. Heterocycles 2005, 65: 1641Reference Ris Wihthout Link - 5c
Fujita M.Qi G.-Z.Verkerk UH.Dzwiniel TL.McDonald R.Stryker JM. Org. Lett. 2004, 6: 2653Reference Ris Wihthout Link - For other reagents, see:
- 5d
Aslam SN.Stevenson PC.Phythian SJ.Veitch NC.Hall DR. Tetrahedron 2006, 62: 4214Reference Ris Wihthout Link - 5e
Lattanzi A.Senatore A.Massa A.Scettri A. J. Org. Chem. 2003, 68: 3691Reference Ris Wihthout Link - 6a
Shen Q.Peng Q.Shao J.-L.Liu X.-L.Huang Z.-H.Pu X.-Z.Ma L.Li Y.-M.Chan ASC.Gu L.-Q. Eur. J. Med. Chem. 2005, 40: 1307Reference Ris Wihthout Link - 6b
Mashraqui SH.Patil MB.Sangvikar Y.Ashraf M.Mistry HD.Daub ETH.Meetsma A. J. Heterocycl. Chem. 2005, 42: 947Reference Ris Wihthout Link - 6c
Jørgensen M.Krebs FC.Bechgaard K. J. Org. Chem. 2000, 65: 8783Reference Ris Wihthout Link - 7a
Rele S.Talukdar S.Banerji A.Chattopadhyay S. J. Org. Chem. 2001, 66: 2990Reference Ris Wihthout Link - 7b
Furstner A.Hupperts A. J. Am. Chem. Soc. 1995, 117: 4468Reference Ris Wihthout Link - 7c
Furstner A.Hupperts A.Rock A.Janssen E. J. Org. Chem. 1994, 59: 5215Reference Ris Wihthout Link - 8a
Yuan Y.Men H.-B.Lee C. J. Am. Chem. Soc. 2004, 126: 14720Reference Ris Wihthout Link - 8b
Katerina C.Miloslav N.Pavel P.Jiri S. Collect. Czech. Chem. Commun. 2000, 65: 1939Reference Ris Wihthout Link - 8c
Jean G.Nicole B.Pierre D. J. Heterocycl. Chem. 1990, 27: 10Reference Ris Wihthout Link - 9a
Duan XF.Zeng J.Lü JW.Zhang ZB. J. Org. Chem. 2006, 71: 9873Reference Ris Wihthout Link - 9b
Duan XF.Zeng J.Lü JW.Zhang ZB. Synthesis 2007, 713Reference Ris Wihthout Link - 9c
Duan XF.Zeng J.Zhang ZB.Zi GF. J. Org. Chem. 2007, 72: 10283Reference Ris Wihthout Link - 10
Duan XF.Feng JX.Zi GF.Zhang ZB. Synthesis 2009, 277 - 11a
Segal R.Ilana MG.Sokoloff S.Zaitschek DV. J. Chem. Soc. C 1967, 2402Reference Ris Wihthout Link - 11b
Schreiber FG.Stevenson R. Chem. Lett. 1975, 1257Reference Ris Wihthout Link - 11c
Schreiber FG.Stevenson R. J. Chem. Soc., Perkin Trans. 1 1976, 1514Reference Ris Wihthout Link - 11d
Teles HL.Hemerly JP.Pauletti PM.Pandolfi JRC.Araujo AR.Valentini SR.Young MCM.Bolzani VS.Silva DHS. Nat. Prod. Res. 2005, 19: 319Reference Ris Wihthout Link - 13
Fürstner A.Davies PW. J. Am. Chem. Soc. 2005, 127: 15024Reference Ris Wihthout Link - 14
Date M.Kawanishi K.Hori T.Watanabe M.Furukawa S. Chem. Pharm. Bull. 1989, 37: 2884 - 15
Farago J.Kotschy A. Synthesis 2009, 85
References
In several of the reactions, a small amount of alkenes formed as byproducts during the cross-coupling which hindered the acid-promoted cyclization of the pinacol products. Although it was not necessary to separate the three pinacols, the alkene by-product was removed by chromatography.