Copper-Catalyzed Ring Opening of Furans as a Concise Route to Polysubstituted Furans under Mild Conditions

Abstract

A range of polysubstituted furans were synthesized from furan derivatives involving copper-catalyzed ring opening of the furan ring. This synthetic method possesses the advantages of readily available starting materials, mild reaction conditions, and short steps.

Key words

polysubstituted furan - ring-opening of furan - ring-opening/rearomatization - copper-catalyzed

• References


For selected reviews, see:
• 1a Keay BA, Hopkins JM, Dibble PW In Comprehensive Heterocyclic Chemistry III . Vol. 3. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 571
• 1b d’Ischia M, Napolitano A, Pezzella A In Comprehensive Heterocyclic Chemistry III . Vol. 3. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 353
• 1c Lipshutz BH. Chem. Rev. 1986; 86: 795

For reviews concerning the dearomatization of furan ring, see:
• 2a Roche SP, Poreo JA. Jr. Angew. Chem., Int. Ed. Engl. 1996; 35: 729
• 2b Bur SK, Padwa A. Chem. Rev. 2004; 104: 2401
• 3a Cagniant P, Cagniant D In Advances in Heterocyclic Chemistry . Vol. 18. Katritzky AR, Boulton AJ. Academic Press; New York: 1975: 337
• 3b Dean FM, Sargent MV. In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon; New York: 1984: 531
• 3c Cacchi S. J. Organomet. Chem. 1999; 576: 42
• 3d Hou XL. H, Cheung Y, Hon TY, Kwan PL, Lo TH, Tong SY, Wong HN. C. Tetrahedron 1998; 54: 1955

For selected references concerning the dearomatization of furans, see:
• 4a Toró A, Deslongchamps P. J. Org. Chem. 2003; 68: 6847
• 4b Liu L, Gao Y, Che C, Wu N, Wang DZ, Li C.-C, Yang Z. Chem. Commun. 2009; 662
• 5a Yim H.-K, Wong HN. C. J. Org. Chem. 2004; 69: 2892
• 5b McDermott PJ, Stockman RA. Org. Lett. 2005; 7: 27
• 5c Georgiou T, Tofi M, Montagnon T, Vassilikogiannakis G. Org. Lett. 2006; 8: 1945
• 5d Zhou X, Wu W, Liu X, Lee C.-S. Org. Lett. 2008; 10: 5525
• 5e Abrams JN, Babu RS, Guo H, Le D, Le J, Osbourn JM. G, O’Doherty A. J. Org. Chem. 2008; 73: 1935
• 5f Bi J, Aggarwal VK. Chem. Commun. 2008; 120
• 5g Pavlakos E, Georgiou T, Tofi M, Montagnon T, Vassilikogiannakis G. Org. Lett. 2009; 11: 4556
• 5h Dong J.-Q, Wong HN. C. Angew. Chem. Int. Ed. 2009; 48: 2351
• 5i Hatano M, Mizuno T, Ishihara K. Chem. Commun. 2010; 46: 5443
• 5j Veits GK, Wenz DR, Read de Alaniz J. Angew. Chem. Int. Ed. 2010; 49: 9484
• 5k Noutsias D, Kouridaki A, Vassilikogiannakis G. Org. Lett. 2011; 13: 1166
• 5l Egan BA, Paradowski M, Thomas LH, Marquez R. Org. Lett. 2011; 13: 2086
• 5m Yin B, Zeng G, Cai C, Ji F, Huang L, Li Z, Jiang H. Org. Lett. 2012; 14: 616
• 5n Yin B, Cai C, Zeng G, Zhang R, Li X, Jiang H. Org. Lett. 2012; 14: 1098
• 6a Benson G. Org. Synth., Coll. Vol. 2 . Wiley; New York: 1943: 220
• 6b Takano S, Otaki S, Ogasawara K. J. Chem. Soc., Chem. Commun. 1983; 1172
• 6c Bezoari MD, Paudler WW. J. Org. Chem. 1980; 45: 4584
• 6d Faragher R, Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1979; 258
• 6e Kurihara T, Harusava S, Hirai J, Yoneda R. J. Chem. Soc., Perkin Trans. 1 1987; 1771
• 7a Butin AV, Stroganova TA, Lodina IV, Krapivin GD. Tetrahedron Lett. 2001; 42: 2031
• 7b Butin AV, Smirnov SK, Stroganova TA, Bender W, Krapivin GD. Tetrahedron 2007; 63: 474
• 8a Gao Y, Wu W.-L, Ye B, Zhou R, Wu Y.-L. Tetrahedron Lett. 1996; 37: 893
• 8b Yin B.-L, Yang Z.-M, Hu T.-S, Wu Y.-L. Synthesis 2003; 1995
• 8c Chen L, Xu H.-H, Yin B.-L, Xiao C, Hu T.-S, Wu Y.-L. J. Agric. Food Chem. 2004; 52: 6719
• 8d Yin B.-L, Lai J.-Q, Zhang Z.-R, Jiang H.-F. Adv. Synth. Catal. 2011; 353: 1961
• 8e Yin B, Huang L, Zhang X, Ji F, Jiang H. J. Org. Chem. 2012; 77: 6365
• 9a Yin B, Zeng G, Cai C, Ji F, Huang L, Li Z, Jiang H. Org. Lett. 2012; 14: 616
• 9b Yin B, Cai C, Zeng G, Zhang R, Li X, Jiang H. Org. Lett. 2012; 14: 1098

For selected examples concerning the synthesis of tetrasubstituted furans, see:
• 10a Fournier J, Arseniyadis S, Cossy J. Angew. Chem. Int. Ed. 2012; 51: 7562
• 10b Yin B, Zeng G, Cai C, Ji F, Huang L, Li Z, Jiang H. Org. Lett. 2012; 14: 616
• 10c Li L, Zhao M.-N, Ren Z.-H, Li J, Guang Z. Synthesis 2012; 44: 6276
• 10d York M. Tetrahedron 2011; 52: 6267
• 10e Zhang X, Lu Z, Fu C, Ma S. J. Org. Chem. 2010; 75: 2589
• 10f Liu W, Jiang H, Zhang M, Qi C. J. Org. Chem. 2010; 75: 966
• 10g Cao H, Jiang H, Yao W, Liu X. Org. Lett. 2009; 11: 1931