K3PO4-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

doi:10.1007/s40242-019-9137-y

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (6): 1002-1007.doi: 10.1007/s40242-019-9137-y

K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

CHEN Zhanguo, WEN Ting, HOU Dan

Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China

收稿日期:2019-05-17 修回日期:2019-07-09 出版日期:2019-12-01 发布日期:2019-11-29
通讯作者: CHEN Zhanguo E-mail:chzhg@snnu.edu.cn
基金资助:
Supported by the Natural Science Foundation of Shaanxi Province, China(No.2009JM2001) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University, China(No.2008CXB009).

K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

CHEN Zhanguo, WEN Ting, HOU Dan

Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China

Received:2019-05-17 Revised:2019-07-09 Online:2019-12-01 Published:2019-11-29
Contact: CHEN Zhanguo E-mail:chzhg@snnu.edu.cn
Supported by:
Supported by the Natural Science Foundation of Shaanxi Province, China(No.2009JM2001) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University, China(No.2008CXB009).

摘要/Abstract

摘要： 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 react 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.

关键词: Cyclopropanation, Multisubstituted cyclopropane derivative, Electron-deficicent alkene, 2-Bromo-1,3-propanedione compound

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 react 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.

Key words: Cyclopropanation, Multisubstituted cyclopropane derivative, Electron-deficicent alkene, 2-Bromo-1,3-propanedione compound

CHEN Zhanguo, WEN Ting, HOU Dan. K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds[J]. 高等学校化学研究, 2019, 35(6): 1002-1007.

CHEN Zhanguo, WEN Ting, HOU Dan. K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds[J]. Chemical Research in Chinese Universities, 2019, 35(6): 1002-1007.

参考文献

[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., Angew. Chem., Int. Ed., 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, (10), 1621
[30] Zheng J. C., Liao W. W., Tang Y., Sun X. L., Dai L.X., 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., Tetrahedron, 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 Universities, 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 A., Seifermann S. M., Bihlmeier A., Muller T., Topic F., Rissanen K., Nieger M., Klopper W., Brase S., Eur. J. Org. Chem., 2013, (35), 7907
[46] Pravst I., Zupan M., Stavber S., Green Chem., 2006, 8(11), 1001

K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 2

编辑推荐

Metrics

本文评价

[1]	JIANG Chang-sheng, LI You-gui, JIANG Chen, WEN Ji-wu, YOU Tian-pa. Asymmetric Cyclopropanation Catalyzed by a Copper-(Schiff-base)Complex with Double Chiral Centers[J]. 高等学校化学研究, 2003, 19(2): 238-239.
[2]	ZHANG X. A., Campbell M. M., Brown, D. W. . Synthetic Studies on 1-Amino-1-Cyclopropane-Carboxylic Acid(Ⅰ)--The Cyclopropanation via Addition-Elimination Reactions[J]. 高等学校化学研究, 1992, 8(4): 377-381.