Recent Advances in Hydroboration of Alkenes Catalyzed by Fe, Co and Ni

doi:10.6023/cjoc201909035

Abstract

The synthesis of alkyl boronic esters has attracted much attention because of their wide applications in organic synthesis, materials and medicines. Transition-metal catalyzed hydroboration of alkenes was one of the most effective methods to construct alkyl boronic esters. Compared with rhodium, ruthenium, palladium, iridium and other precious metal catalysts, iron, cobalt and nickel catalysts were not only low cost, but also they displayed unique reactivity and selectivity. In this paper, the important advances in hydroboration of alkenes catalyzed by iron, cobalt and nickel have been summarized since 1994, including catalytic activity, selectivity and substrate scope of different catalytic systems.

Key words: iron-catalysis, cobalt-catalysis, nickel-catalysis, hydroboration, regio-selectivity

Cite this article

Sun Yue, Guan Rui, Liu Zhaohong, Wang Yeming. Recent Advances in Hydroboration of Alkenes Catalyzed by Fe, Co and Ni[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 899-912.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Brown, H. C.; Singaram, B. Pure Appl. Chem. 1987, 59, 879.
[2] Stymiest, J. L.; Bagutski, V.; French R. M.; Aggarwal, V. K. Nature 2008, 456, 778.
[3] Bagutski, V.; French R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2010, 49, 5142.
[4] Bull, J. A. Angew. Chem., Int. Ed. 2012, 51, 8930.
[5] Mlynarski, S. N.; Karns, A. S.; Morken, J. P. J. Am. Chem. Soc. 2012, 134, 16449.
[6] Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6723.
[7] Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1956, 78, 2582.
[8] Mattraw, H. C.; Erickson, C. E.; Laubengayer, A. W. J. Am. Chem. Soc. 1956, 78, 4901.
[9] McCusker, P. A.; Ashby, E. C.; Makowski, H. S. J. Am. Chem. Soc. 1957, 79, 5179.
[10] Washburn, R. M.; Levens, E.; Albright, C. F.; Billig, F. A.; Cernak, E. S. Adv. Chem. Ser. 1959, 23, 102.
[11] Matteson, D. S.; Liedtke, J. D. J. Am. Chem. Soc. 1965, 87, 1526.
[12] Dhillon, R. S. Hydroboration and Organic Synthesis, Springer Berlin Heidelberg, New York, 2007, pp. 59~99.
[13] Mannig, D.; Noth, H. Angew. Chem., Int. Ed. 1985, 24, 878.
[14] Burgess K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
[15] Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
[16] Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695.
[17] Vogels, C. M.; Westcott, S. A. Curr. Org. Chem. 2005, 9, 687.
[18] Carroll, A.-M.; O'Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609.
[19] Wu, Y.; Shan, C.; Ying, J.; Su, J.; Zhu, J.; Liu, L. L.; Zhao, Y. Green Chem. 2017, 19, 4169.
[20] Ma, D. H.; Jaladi, A. K.; Lee, J. H.; Kim, T. S.; Shin, W. K.; Hwang, H.; An, D. ACS Omega 2019, 4, 15893.
[21] Li, Y.; Cheng, Y.; Shan, C.; Zhang, J.; Xu, D.; Bai, R.; Qu, L.; Lan, Y. Chin. J. Org. Chem. 2018, 38, 1885(in Chinese). (李园园, 程玉华, 单春晖, 张敬, 徐冬冬, 白若鹏, 屈凌波, 蓝宇, 有机化学, 2018, 38, 1885.)
[22] Zhang, L.; Huang, Z. Synlett 2013, 1745.
[23] Obligacion, J. V.; Chirik, P. J. Nat. Rev. Chem. 2018, 2, 15.
[24] Chen, J.; Lu, Z. Org. Chem. Front. 2018, 5, 260.
[25] Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075.
[26] Fan, W.; Li, L.; Zhang, G. J. Org. Chem. 2019, 84, 5987.
[27] Wang, Y.; Li, W.; Che, G.; Bi, X.; Liao, P.; Zhang, Q.; Liu, Q. Chem. Commun. 2010, 46, 6843.
[28] Wang, Y.; Bi, X.; Li, D.; Liao, P.; Wang, Y. Yang, J. Zhang, Q. Liu, Q. Chem. Commun. 2011, 47, 809.
[29] Wang, Y.; Bi, X.; Li, W.; Li, D.; Zhang, Q.; Liu, Q.; Ondon, B. S. Org. Lett. 2011, 13, 1722.
[30] Li, Q.; Wang, Y.; Fang, Z.; Liao, P.; Barry, B.; Che, G.; Bi, X. Synthesis 2013, 609.
[31] Sun, B.; Ma, Q.; Wang, Y.; Zhao, Y.; Liao, P.; Bi, X. Eur. J. Org. Chem. 2014, 34, 7552.
[32] Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
[33] Correa, A.; Mancheno, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108.
[34] Baucer, E. B. Curr. Org. Chem. 2008, 12, 1341.
[35] Greenhalgh, M. D.; Thomas, S. P. Chem. Cat. Chem. 2014, 6, 1520.
[36] Bauer, I.; Knölker, H.-J. Chem. Rev. 2015, 115, 3170.
[37] Mako, T. L.; Byers, J. A. Inorg. Chem. Front. 2016, 3, 766.
[38] Shang, R.; Ilies, L.; Nakamu, E. Chem. Rev. 2017, 117, 9086.
[39] Li, Y.; Hu, Y.; Wu, X. Chem. Soc. Rev. 2018, 47, 172.
[40] Wu, J. Y.; Moreau, B.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 12915.
[41] Cao, Y.; Zhang, Y.; Zhang, L.; Zhang, D.; Leng, X.; Huang, Z. Org. Chem. Front. 2014, 1, 1101.
[42] Zhang, L.; Peng, D.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2013, 52, 3676.
[43] Gilbert-Wilson, R.; Chu, W.-Y.; Rauchfuss, T. B. Inorg. Chem. 2015, 54, 5596.
[44] Espinal-Viguri, M.; Woof, C. R.; Webster, R. L. Chem.-Eur. J. 2016, 22, 11605.
[45] Obligacion, J. V.; Chirik, P. J. Org. Lett. 2013, 15, 2680.
[46] Chen, J.; Xi, T.; Lu, Z. Org. Lett. 2014, 16, 6452.
[47] Tseng, K. T.; Kampf, J. W.; Szymczak, N. K. ACS Catal. 2015, 5, 411.
[48] Zheng, J.; Sortais, J.-B.; Darcel, C. Chem. Cat. Chem. 2014, 6, 763.
[49] Cruz, T. F. C.; Pereira, L. C. J.; Waerenborgh, J. C.; Veiros, L. F.; Gomes. P. T. Catal. Sci. Technol. 2019, 9, 3347.
[50] Greenhalgh, M. D.; Thomas, S. P. Chem. Commun. 2013, 49, 11230.
[51] Agahi, R.; Challinor, A. J.; Carter, N. B.; Thomas, S. P. Org. Lett. 2019, 21, 993.
[52] Liu, Y.; Zhou, Y.; Wang, H.; Qu, J. RSC Adv. 2015, 5, 73705.
[53] Macnair, A. J.; Millet, C. R. P.; Nichol, G. S.; Ironmonger, A.; Thomas, S. P. ACS Catal. 2016, 6, 7217.
[54] Chen, X.; Cheng, Z.; Lu, Z. Org. Lett. 2017, 19, 969.
[55] Chen, C.; Shen, X.; Chen, J.; Hong, X.; Lu, Z. Org. Lett. 2017, 19, 5422.
[56] Zaidlewicz, M.; Meller, J. Tetrahedron Lett. 1997, 38, 7279.
[57] Obligacion, J. V.; Chirik, P. J. J. Am. Chem. Soc. 2013, 135, 19107.
[58] Zhang, L.; Zuo, Z.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2014, 53, 2696.
[59] Ruddy, A. J.; Sydora, O. L.; Small, B. L.; Stradiotto, M.; Turculet, L. Chem. Eur. J. 2014, 20, 13918.
[60] Docherty, J. H.; Peng, J.; Dominey, A. P.; Thomas, S. P. Nat. Chem. 2017, 9, 595.
[61] Ibrahim, A. D.; Entsminger, S. W.; Fout. A. R. ACS Catal. 2017, 7, 3730.
[62] Pang, M.; Wu, C.; Zhuang, X.; Zhang, F.; Su, M.; Tong, Q.; Tung, C.-H.; Wang, W. Organometallics 2018, 37, 1462.
[63] Cruz, T. F. C.; Lopes, P. S.; Pereira, L. C. J.; Veiros, L. F.; Gomes, P. T. Inorg. Chem. 2018, 57, 8146.
[64] Zhang, L.; Zuo, Z.; Wan, X.; Huang, Z. J. Am. Chem. Soc. 2014, 136, 15501.
[65] Chen, J.; Xi, T.; Ren, X.; Cheng, B.; Guo J.; Lu, Z. Org. Chem. Front. 2014, 1, 1306.
[66] Zhang, H.; Lu, Z. ACS Catal. 2016, 6, 6596.
[67] Teo, W. J.; Ge, S. Angew. Chem., Int. Ed. 2018, 57, 12935.
[68] Duvvuri, K.; Dewese, K. R.; Parsutkar, M. M.; Jing, S. M.; Mehta, M. M.; Gallucci, J. C.; RajanBabu, T. V. J. Am. Chem. Soc. 2019, 141, 7365.
[69] Peng, S.; Yang, J.; Liu, G.; Huang, Z. Sci. China Chem. 2019, 62, 336.
[70] Palmer, W. N.; Diao, T.; Pappas, I.; Chirik, P. J. ACS Catal. 2015, 5, 622.
[71] Reilly, S. W.; Webster, C. E.; Hollis, T. K.; Valle, H. U. Dalton Trans. 2016, 45, 2823.
[72] Peng, J.; Docherty, J. H.; Dominey, A. P.; Thomas, S. P. Chem. Commun. 2017, 53, 4726.
[73] Zhang, G.; Wu, J.; Wang, M.; Zeng, H.; Cheng, J.; Neary, M. C.; Zheng, S. Eur. J. Org. Chem. 2017, 2017, 5814.
[74] Zhang, G.; Wu, J.; Li, S.; Cass, S.; Zheng, S. Org. Lett. 2018, 20, 7893.
[75] Verma, P. K.; Sethulekshmi, A. S.; Geetharani, K. Org. Lett. 2018, 20, 7840.
[76] Tamang, S. R.; Bedi, D.; Shafiei-Haghighi, S.; Smith, C. R.; Crawford, C.; Findlater, M. Org. Lett. 2018, 20, 6695.
[77] Chen, X.; Cheng, Z.; Lu, Z. ACS Catal. 2019, 9, 4025.
[78] Scheuermann, M. L.; Johnson, E. J.; Chirik, P. J. Org. Lett. 2015, 17, 2716.
[79] Ogawa, T.; Ruddy, A. J.; Sydora, O. L.; Stradiotto, M.; Turculet, L. Organometallics 2017, 36, 417.
[80] Chen, X.; Cheng, Z.; Guo, J.; Lu, Z. Nat. Comm. 2018, 9, 3939.
[81] Chong, C. C.; Kinjo, R. ACS Catal. 2015, 5, 3238.
[82] Shegavi, M. L.; Bose, S. K. Catal. Sci. Technol. 2019, 9, 3307.
[83] Tamang, S. R.; Findlater, M. J. Org. Chem. 2017, 82, 12857.
[84] Guo, J.; Chen, J.; Lu, Z. Chem. Commun. 2015, 51, 5725.
[85] King, A. E.; Stieber, S. C. E.; Henson, N. J.; Kozimor, S. A.; Scott, B. L.; Smythe, N. C.; Sutton, A. D.; Gordon, J. C. Eur. J. Inorg. Chem. 2016, 2016, 1635.
[86] Zhang, G.; Zeng, H.; Wu, J.; Yin, Z.; Zheng, S.; Fittinger, J. C. Angew. Chem., Int. Ed. 2016, 55, 14369.
[87] Kabalka, G. W.; Narayana, C.; Reddy, N. K. Synth. Commun. 1994, 24, 1019.
[88] Pereira, S.; Srebnik, M. Tetrahedron Lett. 1996, 37, 3283.
[89] Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 5031.
[90] Lillo, V.; Geier, M. J.; Westcott, S. A.; Fernández, E. Org. Biomol. Chem. 2009, 7, 4674.
[91] Ely, R. J.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 2534.
[92] Ely, R. J.; Morken, J. P. Org. Lett. 2010, 12, 4348.
[93] Ely, R. J.; Yu, Z.; Morken, J. P. Tetrahedron Lett. 2015, 56, 3402.
[94] Touney, E. E.; Hoveln, R. V.; Buttke, C. T.; Freidberg, M. D.; Guzei, I. A.; Schomaker, J. M. Organometallics 2016, 35, 3436.
[95] Li, J.-F.; Wei, Z.-Z.; Wang, Y.-Q.; Ye, M. Green Chem. 2017, 19, 4498.
[96] Kamei, T.; Nishino, S.; Shimada, T. Tetrahedron Lett. 2018, 59, 2896.
[97] Vijaykumar, G.; Bhunia, M.; Mandal, S. K. Dalton Trans. 2019, 48, 5779.
[98] Vijaykumar, G.; Pariyar, A.; Ahmed, J.; Shaw, B. K.; Adhikari, D.; Mandal, S. K. Chem. Sci. 2018, 9, 2817.
[99] Haberberger, M.; Enthaler, S. Chem. Asian J. 2013, 8, 50.
[100] Obligacion, J. V.; Neely, J. M., Yazdani, A. N.; Pappas, I.; Chirik, P. J. J. Am. Chem. Soc. 2015, 137, 5855.
[101] Zuo, Z.; Huang, Z. Org. Chem. Front. 2016, 3, 434.
[102] Nakajima, K.; Kato, T.; Nishibayashi, Y. Org. Lett. 2017, 19, 4323.
[103] Gorgas, N.; Alves, L. G.; Stoeger, B.; Martins A. M.; Veiros, L. F.; Kirchner, K. J. Am. Chem. Soc. 2017, 139, 8130.
[104] Ferrand, L.; Lyu, Y.; Rivera-Hernández, A.; Fallon, B. J.; Amatore, M.; Aubert, C.; Petit, M. Synthesis 2017, 49, 3895.
[105] Ben-Daat, H.; Rock, C. L.; Flores, M.; Groy, T. L.; Bowmanb, A. C.; Trovitch, R. J. Chem. Commun. 2017, 53, 7333.
[106] Zuo, Z.; Wen, H.; Liu, G.; Huang, Z. Synlett 2018, 29, 1421.
[107] Li, L.; Liu, E.; Cheng, J.; Zhang, G. Dalton Trans. 2018, 47, 9579.
[108] Wu, J.; Zeng, H.; Cheng, J.; Zheng, S.; Golen, J. A.; Manke, D. R.; Zhang, G. J. Org. Chem. 2018, 83, 16, 9442.
[109] Zhang, G.; Cheng, J.; Davis, K.; Bonifacioa, M. G.; Zajaczkowskia, C. Green Chem. 2019, 21, 1114.
[110] Zhang, G.; Li, S.; Wu, J.; Zeng, H.; Mo, Z.; Davisa, K.; Zheng, S. Org. Chem. Front. 2019, 6, 3228.

铁、钴、镍催化烯烃的硼氢化反应研究进展