Gold-Catalysis: Reactions of Furandialkynes

Abstract

Six furandialkynes were prepared and investigated in gold-catalyzed reactions. Only gold(III) chloride allowed a conversion of the furandialkynes into the corresponding phenol derivative and a further conversion of the ortho-alkynylfurans into benzofurans. Free hydroxy groups in the substrate led to competing hydroalkoxylations to give acylfurans or benzofuran spiroketals.

Key words

alkynes - benzofurans - furans - gold - homogeneous catalysis - spiro compounds

References

• 1a Dyker G. Angew. Chem. Int. Ed.  2000,  39:  4237 ; Angew. Chem. 2000, 112, 4407
• 1b Hashmi ASK. Gold Bull.  2003,  36:  3 
• 1c Hashmi ASK. Gold Bull.  2004,  37:  51 
• 1d Krause N. Hoffmann-Röder A. Org. Biomol. Chem.  2005,  3:  387 
• 1e Hashmi ASK. Angew. Chem. Int. Ed.  2005,  44:  6990 ; Angew. Chem. 2005, 117, 7150
• 1f Hashmi ASK. Hutchings G. Angew. Chem. Int. Ed.  2006,  45:  7896 ; Angew. Chem. 2006, 118, 8064
• 1g Hashmi ASK. Chem. Rev.  2007,  107:  3180 
• 2 Hashmi ASK. Frost TM. Bats JW. J. Am. Chem. Soc.  2000,  122:  11553 
• 3 Martín-Matute B. Cardenas DJ. Echavarren AM. Angew. Chem. Int. Ed.  2001,  40:  4754 ; Angew. Chem. 2001, 113, 4890
• 4 Méndez M. Munoz MP. Nevade C. Cárdenas DJ. Echavarren AM. J. Am. Chem. Soc.  2001,  123:  10511 
• 5 Hashmi ASK. Frost TM. Bats JW. Org. Lett.  2001,  3:  3769 
• 6 Hashmi ASK. Frost TM. Bats JW. Catal. Today  2002,  72:  19 
• 7 Hashmi ASK. Kurpejovic E. Frey W. Bats JW. Tetrahedron  2007,  63:  5879 
• 8 Hashmi ASK. Wölfle M. Ata F. Hamzic M. Salathé R. Frey W. Adv. Synth. Catal.  2006,  348:  2501 
• 9 Hashmi ASK. Wölfle M. Teles JH. Frey W. Synlett  2007,  1747 
• 10 Hashmi ASK. Ding L. Fischer P. Bats JW. Frey W. Chem. Eur. J.  2003,  9:  4339 
• 11 Hashmi ASK. Grundl L. Tetrahedron  2005,  61:  6231 
• 12 Hashmi ASK. Rudolph M. Bats JW. Frey W. Rominger F. Oeser T. Chem. Eur. J.  2008,  14: in press
• 13 Hashmi ASK. Weyrauch JP. Rudolph M. Kurpejovic E. Angew. Chem. Int. Ed.  2004,  43:  6545 ; Angew. Chem. 2004, 116, 6707
• 14 Hashmi ASK. Blanco MC. Kurpejovic E. Frey W. Bats JW. Adv. Synth. Catal.  2006,  348:  709 
• 15 Hashmi ASK. Haufe P. Schmid C. Rivas Nass A. Frey W. Chem. Eur. J.  2006,  12:  5376 
• 16 Hashmi ASK. Salathé R. Frey W. Chem. Eur. J.  2006,  12:  6991 
• 17 Hashmi ASK. Ata F. Kurpejovic E. Huck J. Rudolph M. Top. Catal.  2007,  44:  245 
• 18 Hashmi ASK. Rudolph M. Siehl H.-U. Tanaka M. Bats JW. Frey W. Chem. Eur. J.  2008,  14:  3703 
• 19 Hashmi ASK. Rudolph M. Weyrauch JP. Wölfle M. Frey W. Bats JW. Angew. Chem. Int. Ed.  2005,  44:  2798 ; Angew. Chem. 2005, 117, 2858
• 20 Hashmi ASK. Weyrauch JP. Kurpejovic E. Frost TM. Miehlich B. Frey W. Bats JW. Chem. Eur. J.  2006,  12:  5806 
• 21 Hashmi ASK. Kurpejovic E. Wölfle M. Frey W. Bats JW. Adv. Synth. Catal.  2007,  349:  1743 
• 22a Monteiro N. Balme G. Synlett  1998,  746 
• 22b Yoshida M. Morishita Y. Fujita M. Ihara M. Tetrahedron  2005,  61:  4381 
• 22c Li X. Chianese AR. Vogel T. Crabtree RH. Org. Lett.  2005,  7:  5437 
• 22d Belting V. Krause N. Org. Lett.  2006,  8:  4489 
• 24 Gagosz F. Org. Lett.  2005,  7:  4129 

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CCDC 631589 (7c), 687063 (7g), 631588 (7h), 631590 (10e) and 687064 (15g) contain the supplementary crystallographic data for this paper. These data can be obtained online free of charge or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; or [e-mail]