Potassium Persulfate Mediated Oxidative Radical Cyclization of 1,3-Dicarbonyl Compounds with Styrenes for the Synthesis of Dihydrofurans

Abstract

A potassium persulfate promoted tandem radical addition/cyclization of 1,3-dicarbonyl compounds with styrenes has been developed. This transition-metal-free procedure provides an efficient approach to a diverse set of substituted dihydrofurans in moderate to good yields.

Key words

dicarbonyl compounds - styrenes - free radicals - cyclizations - tandem reactions - furans

• References


For selected examples, see:
• 1a Wang X, Nakagawa-Goto K, Bastow KF, Don M.-J, Lin Y.-L, Wu T.-S, Lee K.-H. J. Med. Chem. 2006; 49: 5631
• 1b Yang S.-W, Chan T.-M, Terracciano J, Boehm E, Patel R, Chen G, Loebenberg D, Patel M, Gullo V, Pramanik B, Chu M. J. Nat. Prod. 2009; 72: 484
• 1c Koike T, Takai T, Hoashi Y, Nakayama M, Kosugi Y, Nakashima M, Yoshikubo S.-i, Hirai K, Uchikawa O. J. Med. Chem. 2011; 54: 4207
• 1d Zhang Y, Zhong H, Wang T, Geng D, Zhang M, Li K. Eur. J. Med. Chem. 2012; 48: 69
• 1e Sugimoto K, Tamura K, Ohta N, Tohda C, Toyooka N, Nemoto H, Matsuya Y. Bioorg. Med. Chem. Lett. 2012; 22: 449
• 1f Somerville MJ, Katavic PL, Lambert LK, Pierens GK, Blanchfield JT, Cimino G, Mollo E, Gavagnin M, Banwell MG, Garson MJ. J. Nat. Prod. 2012; 75: 1618

For reviews, see:
• 2a Iqbal J, Bhatia B, Nayyar NK. Chem. Rev. 1994; 94: 519
• 2b Snider BB. Chem. Rev. 1996; 96: 339
• 2c Godoi B, Schumacher RF, Zeni G. Chem. Rev. 2011; 111: 2937
• 2d Le Bras J, Muzart J. Chem. Soc. Rev. 2014; 43: 3003
• 2e Zimmer R, Reissig H.-U. Chem. Soc. Rev. 2014; 43: 2888
• 3a Baciocchi E, Ruzziconi R. J. Org. Chem. 1991; 56: 4772
• 3b Bar G, Parsons AF, Thomas CB. Chem. Commun. 2001; 1350
• 3c Huang J.-W, Shi M. J. Org. Chem. 2005; 70: 3859
• 3d Yuan W, Wei Y, Shi M. Tetrahedron 2011; 67: 7139
• 3e Yao C, Wang Y, Li T, Yu C, Li L, Wang C. Tetrahedron 2013; 69: 10593
• 3f Asouti A, Hadjiarapoglou LP. Tetrahedron Lett. 1998; 39: 9073
• 3g Ye Y, Wang L, Fan R. J. Org. Chem. 2010; 75: 1760
• 3h Kalpogiannaki D, Martini C.-I, Nikopoulou A, Nyxas JA, Pantazi V, Hadjiarapoglou LP. Tetrahedron 2013; 69: 1566
• 4a Ma S, Zheng Z, Jiang X. Org. Lett. 2007; 9: 529
• 4b Deng Y, Yu Y, Ma S. J. Org. Chem. 2008; 73: 585
• 4c Deng Y, Shi Y, Ma S. Org. Lett. 2009; 11: 1205
• 4d Naveen T, Kancherla R, Maiti D. Org. Lett. 2014; 16: 5446
• 4e Lv L, Lu S, Guo Q, Shen B, Li Z. J. Org. Chem. 2015; 80: 698
• 4f Guo L.-N, Wang S, Duan X.-H, Zhou S.-L. Chem. Commun. 2015; 51: 4803
• 5a Yang Z, Fan M, Mu R, Liu W, Liang Y. Tetrahedron 2005; 61: 9140
• 5b Cao W, Zhang H, Chen J, Zhou X, Shao M, McMills MC. Tetrahedron 2008; 64: 163
• 5c Wang Q.-F, Hou H, Hui L, Yan C.-G. J. Org. Chem. 2009; 74: 7403
• 5d Chen Z, Zhang J, Chen J, Deng H, Shao M, Zhang H, Cao W. Tetrahedron 2010; 66: 6181
• 5e Chagarovsky AO, Budynina EM, Ivanova OA, Villemson EV, Rybakov VB, Trushkov IV, Melnikov MY. Org. Lett. 2014; 16: 2830
• 6a Funayama A, Satoh T, Miura M. J. Am. Chem. Soc. 2005; 127: 15354
• 6b Horita A, Tsurugi H, Funayama A, Satoh T, Miura M. Org. Lett. 2007; 9: 2231

For reviews, see:
• 7a Mousseau JJ, Charette AB. Acc. Chem. Res. 2013; 46: 412
• 7b Sun C.-L, Shi Z.-J. Chem. Rev. 2014; 114: 9219

For selected examples, see:
• 8a Thu H.-Y, Yu W.-Y, Che C.-M. J. Am. Chem. Soc. 2006; 128: 9048
• 8b Seiple IB, Su S, Rodriguez RA, Gianatassio R, Fujiwara Y, Sobel AL, Baran PS. J. Am. Chem. Soc. 2010; 132: 13194
• 8c Chu L, Yue X, Qing F.-L. Org. Lett. 2010; 12: 1644
• 8d Lou S.-J, Xu D.-Q, Shen D.-F, Wang Y.-F, Liu Y.-K, Xu Z.-Y. Chem. Commun. 2012; 48: 11993
• 8e Shi Z, Glorius F. Chem. Sci. 2013; 4: 829
• 8f Xie Z, Cai Y, Hu H, Lin C, Jiang J, Chen Z, Wang L, Pan Y. Org. Lett. 2013; 15: 4600
• 9a Wang H, Guo L.-N, Duan X.-H. Org. Lett. 2013; 15: 5254
• 9b Li Y.-M, Wei X.-H, Li X.-A, Yang S.-D. Chem. Commun. 2013; 49: 11701
• 9c Li Y.-M, Shen Y, Chang K.-J, Yang S.-D. Tetrahedron 2014; 70: 1991
• 9d Wei W, Wen J, Yang D, Du J, You J, Wang H. Green Chem. 2014; 16: 2988
• 9e Wei W, Wen J, Yang D, Liu X, Guo M, Dong R, Wang H. J. Org. Chem. 2014; 79: 4225
• 9f Laha JK, Tummalapalli KS. S, Gupta A. Org. Lett. 2014; 16: 4392
• 9g Yang H, Duan X.-H, Zhao J.-F, Guo L.-N. Org. Lett. 2015; 17: 1998
• 10a Mendenhall GD, Protasiewicz JD, Brown CE, Ingold KU, Lusztyk J. J. Am. Chem. Soc. 1994; 116: 1718
• 10b Yamamoto Y, Ohno M, Eguchi S. J. Org. Chem. 1996; 61: 9264
• 10c Cui X, Xu X, Wojtas L, Kim MM, Zhang XP. J. Am. Chem. Soc. 2012; 134: 19981
• 10d Jiang H, Cheng Y, Zhang Y, Yu S. Org. Lett. 2013; 15: 4884
• 10e Liu D, Tang S, Yi H, Liu C, Qi X, Lan Y, Lei A. Chem. Eur. J. 2014; 20: 15605