K₃PO₄-Promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-Propanedione Compounds

Abstract

An easy and efficient method for the synthesis of multisubstituted cyclopropane derivatives from electron-deficicent alkenes with 2-bromo-1,3-propanedione compounds was described. For this method, ethyl α-cyanocinnamate derivatives 1 and β,β-dicyanostyrene derivatives 4 can all smoothly reacted with 2-bromo-1,3-propanedione compounds 2 to afford the corresponding multisubstituted cyclopropane derivatives 3 and 5 in good to excellent yields(up to 100%) promoted by anhydrous K₃PO₄ in DMF at room temperature, respectively. A possible mechanism of this reaction was proposed. Structures of all the products were confirmed by ¹H NMR, ¹³C NMR and HRMS.

Keywords

Cyclopropanation / Multisubstituted cyclopropane derivative / Electron-deficicent alkene / 2-Bromo-1,3-propanedione compound

References

[1] Lautens M, Klute W, Tam W. Chem. Rev., 1996, 96(1): 49.

[2] Carson C A, Kerr M A. Chem. Soc. Rev., 2009, 38(11): 3051.

[3] Chen D Y K, Pouwer R H, Richard J A. Chem. Soc. Rev., 2012, 41(13): 4631.

[4] Kim H Y, Walsh P J. Acc. Chem. Res., 2012, 45(9): 1533.

[5] Pan L, Liu X H, Shi Y X, Wang B L, Wang S H, Li B J, Li Z M. Chem. Res. Chinese Universities, 2010, 26(3): 389.

[6] Faust R. Angew Chem. Int. Ed., 2001, 40(12): 2251.

[7] Donaldson W A. Tetrahedron, 2001, 57(41): 8589.

[8] Little R D, Dawson J R. J. Am. Chem. Soc., 1978, 100(14): 4607.

[9] Little R D, Dawson J R. Tetrahedron Lett., 1980, 21(27): 2609.

[10] Caine D. Tetrahedron, 2001, 57(14): 2643.

[11] Warner D T. J. Org. Chem., 1959, 24: 1536.

[12] McCoy L L. J. Org. Chem., 1964, 29(1): 240.

[13] Wong H N C, Hon M Y, Tse C W, Yip Y C, Tanko J, Hudlicky T. Chem. Rev., 1989, 89(1): 165.

[14] Reissig H U, Zimmer R. Chem. Rev., 2003, 103(4): 1151.

[15] Wurz R P, Charette A B. Org. Lett., 2005, 7(12): 2313.

[16] Carson C A, Kerr M A. Chem. Soc. Rev., 2009, 38(11): 3051.

[17] Simone F. D., Waser J., Synthesis, 2009, (20), 3353

[18] Lebel H, Marcoux J F, Molinaro C, Charette A B. Chem. Rev., 2003, 103(4): 977.

[19] Rubin M, Rubina M, Gevorgyan V. Chem. Rev., 2007, 107(7): 3117.

[20] Rubin M., Rubina M., Gevorgyan V., Synthesis, 2006, (8), 1221

[21] Long J, Yuan Y, Shi Y. J. Am. Chem. Soc., 2003, 125(45): 13632.

[22] Aggarwal V K, Fang G Y, Meek G. Org. Lett., 2003, 5(23): 4417.

[23] Kim H Y, Lurain A E, Garcia-Garcia P, Carroll P J, Walsh P J. J. Am. Chem. Soc., 2005, 127(38): 13138.

[24] Son J B, Hwang M H, Lee W, Lee D H. Org. Lett., 2007, 9(20): 3897.

[25] Davoren J E, Martin S F. J. Am. Chem. Soc., 2007, 129(3): 510.

[26] Qian D, Hu H, Liu F, Tang B, Ye W, Wang Y, Zhang J. Int. Ed. Angew. Chem., 2014, 53(50): 13751.

[27] Qian D, Zhang J. Chem. Commun., 2011, 47(39): 11152.

[28] Pohlman M, Kazmaier U. Org. Lett., 2003, 5(15): 2631.

[29] Huang K, Huang Z Z. Synlett., 2005, 1621.

[30] Zheng J C, Liao W W, Tang Y, Sun X L, Dai LX. J. Am. Chem. Soc., 2005, 127(35): 12222.

[31] Aggarwal V K, Grange E. Chem. Eur. J., 2006, 12(2): 568.

[32] Kawai D, Kawasumi K, Miyahara T, Hirashita T, Araki S. Tetra-hedron, 2009, 65(50): 10390.

[33] Gololobov Y G, Nesmeyanov A N, Lysenko V P, Boldeskul I E. Tetrahedron, 1987, 43(12): 2609.

[34] Padwa A, Ku H. J. Org. Chem., 1980, 45(19): 3756.

[35] Zhang Y B, An Y, Sun J, Ding A S, Wang Y, Rios R, Guo H. Tetrahedron Lett., 2015, 56(46): 6499.

[36] Zhang Y B, Qian R, Zheng X L, Zeng Y, Sun J, Chen Y Y, Ding A S, Guo H. Chem. Commun., 2015, 51(1): 54.

[37] Kuang Y L, Shen B, Dai L, Yao Q, Liu X H, Lin L L, Feng X M. Chem. Sci., 2018, 9(3): 688.

[38] Chen Z G, Xia W, Liu D, Liu Y L, Du M F, Cao C X. J. Chin. Chem. Soc., 2016, 63(2): 158.

[39] Chen Z G, Liu Y L, Hu J L, Liu D. Chem. Res. Chinese Univer-sities, 2015, 31(1): 65.

[40] Chen Z G, Li Y N, Zhou J M, Wang D, Ge M. Chem. Res. Chinese Universities, 2014, 30(2): 266.

[41] Chen Z G, Wen H, Li W L, Zhou J M, Hu J L, Xia W. J. Hetero. Chem., 2014, 51(3): 794.

[42] Chen Z G, Wei J F, Wang M Z, Zhou L Y, Zhang C J, Shi X Y. Adv. Synth. Catal., 2009, 351(14/15): 2358.

[43] Sun Q, Shi L X, Ge Z M, Cheng T M, Li R T. Chin. J. Chem., 2005, 23(6): 745.

[44] Tu S J, Rong L C, Gao Y, Guo S M, Lu S H, Yang X J. Chin. J. Org. Chem., 2002, 22(5): 364.

[45] Giovannitti Alexander, Seifermann Stefan M., Bihlmeier Angela, Muller Thierry, Topic Filip, Rissanen Kari, Nieger Martin, Klopper Wim, Bräse Stefan. Single and Multiple Additions of Dibenzoylmethane onto Buckminsterfullerene. European Journal of Organic Chemistry, 2013, 2013(35): 7907-7913.

[46] Pravst I, Zupan M, Stavber S. Green Chem., 2006, 8(11): 1001.