1,1-二溴-1-烯烃在有机合成中的研究进展

doi:10.6023/cjoc201708034

摘要/Abstract

1，1-二溴-1-烯烃作为一类重要的有机合成原料和中间体，已被应用于C—C、C—N、C—O、C—P和C—S键的构建.二溴烯烃分子中包含一对活泼的C—Br键，使其在制备溴代烯烃、溴代炔烃、端炔和通过经典的偶联反应制备多取代的烯烃、内炔和稠环化合物等的反应中应用广泛.综述了1，1-二溴-1-烯烃在有机合成中的研究进展.

关键词: 1,1-二溴-1-烯烃, 碳-溴键, 交叉偶联, 烯烃, 稠环化合物

As one type of organic synthetic materials and intermediates, 1, 1-dibromo-1-alkenes have been widely researched in C-C, C-N, C-O, C-P, and C-S bond formations. The couple of C-Br bonds in the molecule makes it reactive to afford bromoalkenes, bromoalkynes, terminal alkynes, and to prepare poly-substituted alkenes, fused aromatic rings and internal alkynes through coupling reactions. Various organic reactions with 1, 1-dibromo-1-alkenes as the starting materials are mainly reviewed.

Key words: 1,1-dibromo-1-alkene, C-Br bond, cross coupling, alkenes, fused aromatic compounds

引用此文

赵明, 纪原. 1,1-二溴-1-烯烃在有机合成中的研究进展[J]. 有机化学, 2018, 38(2): 401-415.

Zhao Ming, Ji Yuan. Progress on Synthetic Applications of 1,1-Dibromo-1-alkenes[J]. Chin. J. Org. Chem., 2018, 38(2): 401-415.

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参考文献

[1] (a) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
(b) Desai, N. B.; Mckelvie, N.; Ramirez, F. J. Am. Chem. Soc. 1962, 84, 1745.
[2] Fang, Y. Q.; Lifchits, O.; Lautens, M. Synlett 2008, 413.
[3] Bhorge, Y. R.; Chang, C. T.; Chang, S. H.; Yan, T. H. Eur. J. Org. Chem. 2012, 2012, 4805.
[4] Korotchenko, V. N.; Shastin, A. V.; Nenajdenko, V. G.; Balenkova, E. S. Org. Biomol. Chem. 2003, 1,1906.
[5] Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett 2004, 819.
[6] Pawluc, P.; Hreczycho, G.; Walkowiak, J.; Marciniec, B. Synlett 2007, 2061.
[7] Li, P.; Alper, H. J. Org. Chem. 1986, 51, 4354.
[8] Ratovelomana, V.; Rollin, Y.; Gebehenne, C.; Gosmini, C.; Perichon, J. Tetrahedron Lett. 1994, 35, 4777.
[9] Okutani, M.; Mori, Y. J. Org. Chem. 2008, 74, 442.
[10] Krishna Moodapelly, S.; Sharma, G. V. M.; Ramana Doddi, V. Adv. Synth. Catal. 2017, 359, 1535.
[11] Zhao, M.; Kuang, C. X.; Yang, Q.; Cheng, X. Z. Tetrahedron Lett. 2011, 52, 992.
[12] Liu, S. H.; Chen, X. B.; Hu, Y. W.; Yuan, L. Q.; Chen, S. H.; Wu, P.; Wang, W.; Zhang, S. L.; Zhang, W. Adv. Synth. Catal. 2015, 357, 553.
[13] Morri, A. K.; Thummala, Y.; Doddi, V. R. Org. Lett. 2015, 17, 4640.
[14] Uenishi, J. I.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965.
[15] Fakhfakh, M. A.; Franck, X.; Hocquemiller, R.; Figadère, B. J. Organomet. Chem. 2001, 624, 131.
[16] Xu, H.; Gu, S.; Chen, W.; Li, D.; Dou, J. J. Org. Chem. 2011, 76, 2448.
[17] Zhao, M.; Ming, L.; Tang, J.; Zhao, X. Org. Lett. 2016, 18, 416.
[18] Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1981, 46, 3745.
[19] Ranu, B. C.; Samanta, S.; Guchhait, S. K. J. Org. Chem. 2001, 66, 4102.
[20] Kuang, C. X.; Senboku, H.; Tokuda, M. Tetrahedron 2002, 58, 1491.
[21] Wang, L.; Li, P. H.; Xie, Y. Y.; Ding, Y. B. Synlett 2003, 1137.
[22] Horibe, H.; Kondo, K.; Okuno, H.; Aoyama, T. Synthesis-Stuttgart 2004, 986.
[23] Li, Y. H.; Lu, L.; Zhao, X. M. Org. Lett. 2004, 6, 4467.
[24] Shen, W.; Wang, L. J. Org. Chem. 1999, 64, 8873.
[25] Stille, J. K. Angew. Chem., Int. Ed. 1986, 25, 508.
[26] Shen, W. Synlett 2000, 737.
[27] Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
[28] Riveiros, R.; Saya, L.; Sestelo, J. P.; Sarandeses, L. A. Eur. J. Org. Chem. 2008, 1959.
[29] Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 763.
[30] Ramana, C.; Kishore Reddy, B.; Nageswara Reddy, C.; Gonnade, R.; Gurjar, M. Synlett 2007, 127.
[31] Gu, S.; Xu, H.; Zhang, N.; Chen, W. Chem. Asian J. 2010, 5, 1677.
[32] Oh, C. H.; Lim, Y. M. Bull. Korea Chem. Soc. 2002, 23, 663.
[33] Zhu, Y.; Sun, P.; Yang, H. L.; Lu, L. H.; Yan, H.; Creus, M.; Mao, J. C. Eur. J. Org. Chem. 2012, 4831.
[34] Voyer, N.; Cardinal, S. Synthesis 2016, 48, 1202.
[35] Ogasawara, M.; Ikeda, H.; Hayashi, T. Angew. Chem. 2000, 112, 1084.
[36] Zeng, X.; Qian, M.; Hu, Q.; Negishi, E. -I. Angew. Chem., Int. Ed. 2004, 43, 2259.
[37] Shi, J.; Zeng, X.; Negishi, E. -I. Org. Lett. 2003, 5, 1825.
[38] Uenishi, J.; Iwamoto, T.; Ohmi, M. Tetrahedron Lett. 2007, 48, 1237.
[39] Yan, J. C.; Wang, Z. Y.; Wang, L. J. Chem. Res., Synop. 2004, 71.
[40] (a) Chelucci, G.; Capitta, F.; Baldino, S. Tetrahedron 2008, 64, 10250.
(b) Chelucci, G.; Capitta, F.; Baldino, S.; Pinna, G. A. Tetrahedron Lett. 2007, 48, 6514.
[41] Rahimi, A.; Schmidt, A. Synthesis-Stuttgart 2010, 2621.
[42] Liu, J. D.; Dai, F. L.; Yang, Z. Y.; Wang, S. Z.; Xie, K.; Wang, A. W.; Chen, X.; Tan, Z. Tetrahedron Lett. 2012, 53, 5678.
[43] Yan, H.; Lu, L.; Sun, P.; Zhu, Y.; Yang, H.; Liu, D.; Rong, G.; Mao, J. RSC Adv. 2013, 3, 377.
[44] Rao, M. L.; Jadhav, D. N.; Dasgupta, P. Org. Lett. 2010, 12, 2048.
[45] Rao, M. L. N.; Dasgupta, P.; Murty, V. N. RSC Adv. 2015, 5, 24834.
[46] Berciano, B. P.; Lebrequier, S.; Besselievre, F.; Piguel, S. Org. Lett. 2010, 12, 4038.
[47] Aziz, J.; Baladi, T.; Piguel, S. J. Org. Chem. 2016, 81, 4122.
[48] Reddy, G. C.; Balasubramanyam, P.; Salvanna, N.; Das, B. Eur. J. Org. Chem. 2012, 471.
[49] Shen, C.; Yang, Y. Z.; Liu, Z. X.; Zhang, Y. H. Synth. Commun. 2014, 44, 1970.
[50] Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 2857.
[51] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467.
[52] Lee, H. B.; Huh, D. H.; Oh, J. S.; Min, G. H.; Kim, B. H.; Lee, D. H.; Hwang, J. K.; Kim, Y. G. Tetrahedron 2001, 57, 8283.
[53] Rao, M. L. N.; Dasgupta, P.; Ramakrishna, B. S.; Murty, V. N. Tetrahedron Lett. 2014, 55, 3529.
[54] Yan, J. C.; Wang, L. Synth. Commun. 2005, 35, 2333.
[55] Coste, A.; Couty, F.; Evano, G. Synthesis-Stuttgart 2010, 1500.
[56] Jin, H.; Kuang, C. X. Chin. J. Chem. 2011, 29, 592.
[57] Huang, Z.; Shang, R.; Zhang, Z. R.; Tan, X. D.; Xiao, X.; Fu, Y. J. Org. Chem. 2013, 78, 4551.
[58] Ye, S.; Yang, X.; Wu, J. Chem. Commun. 2010, 46, 2950.
[59] Bryan, C. S.; Lautens, M. Org. Lett. 2010, 12, 2754.
[60] Nicolaus, N.; Franke, P. T.; Lautens, M. Org. Lett. 2011,13, 4236.
[61] (a) Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381.
(b) Jouvin, K.; Coste, A.; Bayle, A.; Legrand, F.; Karthikeyan, G.; Tadiparthi, K.; Evano, G. Organometallics 2012, 31, 7933.
[62] Coste, A.; Couty, F.; Evano, G. Org. Lett. 2009, 11, 4454.
[63] Das, B.; Salvanna, N.; Reddy, G. C.; Balasubramanyam, P. Tetra-hedron Lett. 2011, 52, 6497.
[64] Wang, M. G.; Wu, J.; Shang, Z. C. Synlett 2012, 23, 589.
[65] Huh, D. H.; Ryu, H.; Kim, Y. G. Tetrahedron 2004, 60, 9857.
[66] Fayol, A.; Fang, Y. Q.; Lautens, M. Org. Lett. 2006, 8, 4203.
[67] Fang, Y. Q.; Lautens, M. J. Org. Chem. 2008, 73, 538.
[68] Vieira, T. O.; Meaney, L. A.; Shi, Y. L.; Alper, H. Org. Lett. 2008, 10, 4899.
[69] Jiang, B. S.; Tao, K. M.; Shen, W.; Zhang, J. C. Tetrahedron Lett. 2010, 51, 6342.
[70] Shen, W.; Kohn, T.; Fu, Z.; Jiao, X.; Lai, S. J.; Schmitt, M. Tetrahedron Lett. 2008, 49, 7284.
[71] Tao, K. M.; Zheng, J. L.; Liu, Z. G.; Shen, W.; Zhang, J. C. Tetrahedron Lett. 2010, 51, 3246.
[72] Zhang, A. M.; Zheng, X. L.; Fan, J. F.; Shen, W. Tetrahedron Lett. 2010, 51, 828.
[73] Sun, C.; Xu, B. J. Org. Chem. 2008, 73, 7361.
[74] Taylor, R.; Beltrán-Rodil, S.; Edwards, M.; Pugh, D.; Reid, M. Synlett 2009, 602.
[75] Wang, Z. J.; Yang, J. G.; Yang, F.; Bao, W. Org. Lett. 2010, 12, 3034.
[76] Wang, Z. J.; Yang, F.; Lv, X.; Bao, W. J. Org. Chem. 2011, 76, 967.
[77] Xu, H.; Zhang, Y.; Huang, J. Q.; Chen, W. Z. Org. Lett. 2010, 12, 3704.
[78] Kiruthika, S. E.; Perumal, P. T. Org. Lett. 2014, 16, 484.
[79] Sayyad, M.; Wani, I. A.; Tiwari, D. P.; Ghorai, M. K. Eur. J. Org. Chem. 2017, 2017, 2369.
[80] Shen, W.; Kunzer, A. Org. Lett. 2002, 4, 1315.
[81] Ye, W.; Mo, J.; Zhao, T.; Xu, B. Chem. Commun. (Camb. ) 2009, 45, 3246.
[82] Wang, L.; Li, P. H.; Yan, J. C.; Wu, Z. Z. Tetrahedron Lett. 2003, 44, 4685.
[83] Zhao, M.; Kuang, C. X.; Cheng, X. Z.; Yang, Q. Chin. Chem. Lett. 2011, 22, 571.
[84] Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652.
[85] Murahashi, S. I.; Yamamura, M.; Yanagisawa, K. I.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.
[86] Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christol, H. J. Org. Chem. 1986, 51, 875.
[87] Jin, H.; Yang, Y. W.; Kuang, C. X.; Yang, Q. Synlett 2011, 2886.
[88] Ni, Z.; Wang, S.; Mao, H.; Pan, Y. Tetrahedron Lett. 2012, 53, 3907.
[89] Perin, G.; Roehrs, J. A.; Hellwig, P. S.; Stach, G.; Barcellos, T.; Lenardão, E. J.; Jacob, R. G.; Luz, E. Q. ChemistrySelect 2017, 2, 4561.
[90] Newman, S. G.; Aureggi, V.; Bryan, C. S.; Lautens, M. Chem. Commun. 2009, 5236.
[91] Chen, W.; Zhang, Y.; Zhang, L.; Wang, M.; Wang, L. Chem Commun. 2011, 47, 10476.
[92] (a) Liu, J.; Chen, W.; Ji, Y.; Wang, L. Adv. Synth. Catal. 2012, 354, 1585.
(b) Zhou, W.; Chen, W.; Wang, L. Org. Biomol. Chem. 2012, 10, 4172.
[93] Qin, X.; Cong, X.; Zhao, D.; You, J.; Lan, J. Chem. Commun. 2011, 47, 5611.
[94] Fan, X. S.; He, Y.; Zhang, X. Y.; Guo, S. G.; Wang, Y. Y. Tetrahedron 2011, 67, 6369.
[95] Liu, J. M.; Zhang, N. F.; Yue, Y. Y.; Wang, D.; Zhang, Y. L.; Zhang, X.; Zhuo, K. L. RSC Adv. 2013, 3, 3865.
[96] Liu, J.; Zhang, X.; Shi, L.; Liu, M.; Yue, Y.; Li, F.; Zhuo, K. Chem. Commun. 2014, 50, 9887.
[97] Lera, M.; Hayes, C. J. Org. Lett. 2000, 2, 3873.
[98] Wang, Y.; Gan, J.; Liu, L.; Yuan, H.; Gao, Y.; Liu, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 3678.
[99] Evano, G.; Tadiparthi, K.; Couty, F. Chem. Commun. 2011, 47, 179.
[100] Liu, L.; Wang, Y. L.; Zeng, Z. P.; Xu, P. X.; Gao, Y. X.; Yin, Y. W.; Zhao, Y. F. Adv. Synth. Catal. 2013, 355, 659.
[101] Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2001, 40, 790.
[102] Webber, R.; Peglow, T. J.; Nobre, P. C.; Barcellos, A. M.; Roehrs, J. A.; Schumacher, R. F.; Perin, G. Tetrahedron Lett. 2016, 57, 4128.