过渡金属催化去官能团化反应研究进展

doi:10.6023/cjoc202002038

摘要/Abstract

官能团是决定有机化合物化学性质的原子或原子团，在有机合成化学中常常扮演着导向基团的角色.去官能团化也就是将一个官能团较多的底物，通过化学方法使之成为官能团较少的化合物.去官能团化在解决环境问题、应对资源短缺问题以及生物质降解等方面有积极的应用.但由于化学键键能的存在，化学键的断裂需要能量，去官能团化常常通过加热、加酸或加碱才能实现.近年来，去官能团化一直向着更绿色、更可持续的方向进行.金属催化为去官能团化提供了一种新的途径.总结了近年来不同金属介导的去官能团化反应在有机合成中的应用及其催化反应机理.

关键词: 过渡金属, 去官能团化, 质子化, 选择性

Functional groups are atoms or groups that determine the chemical properties of organic compounds. It often plays the role of guiding group in organic synthesis chemistry. Defunctionalization is the chemical transformation of a substrate with more functional groups into a compound with fewer functional groups, which has positive applications in solving environmental problems, resource shortage and biomass degradation. But due to the bond energy, heating, acid or base are often involved in defunctionalization. In recent years, defunctionalization has been moving toward a greener and more sustainable direction. Metal catalysis provides a new way for defunctionalization. The recent applications of different metal-mediated defunctionalization in organic synthesis and their mechanism are summarized.

Key words: transition metal, defunctionalization, protonation, selectivity

引用此文

董晓娟, 金伟伟, 刘晨江. 过渡金属催化去官能团化反应研究进展[J]. 有机化学, 2020, 40(7): 1860-1873.

Dong Xiaojuan, Jin Weiwei, Liu Chenjiang. Recent Advances in Transition-Metal Catalyzed Defunctionalization Reaction[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1860-1873.

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参考文献

[1] Modak, A.; Maiti, D. Org. Biomol. Chem. 2016, 14, 21.
[2] Verduyckt, J.; Van Hoof, M.; De Schouwer, F.; Wolberg, M.; Kurttepeli, M.; Eloy, P.; Gaigneaux, E. M.; Bals, S.; Kirschhock, C. E. A.; De Vos, D. E. ACS Catal. 2016, 6, 7303.
[3] Ferrini, P.; Chesi, C.; Parkin, N.; Rinaldi, R. Faraday Discuss. 2017, 202, 403.
[4] Takise, R.; Muto, K.; Yamaguchi, J. Chem. Soc. Rev. 2017, 46, 5864.
[5] Matsubara, S.; Yokota, Y.; Oshima, K. Org. Lett. 2004, 6, 2071.
[6] Dickstein, J. S.; Mulrooney, C. A.; O'Brien, E. M.; Morgan, B. J.; Kozlowski, M. C. Org. Lett. 2007, 9, 2441.
[7] Ladwein, K. I.; Jung, M. Angew. Chem., Int. Ed. 2011, 50, 1214
[8] Modak, A.; Naveen, T.; Maiti, D. Chem. Commun. 2013, 49, 252.
[9] Modak, A.; Deb, A.; Patra, T.; Rana, S.; Maity, S.; Maiti, D. Chem. Commun. 2012, 48, 4253.
[10] Akanksha; Maiti, D. Green Chem. 2012, 14, 2314.
[11] (a) Huang, Y.-B.; Yang, Z.; Chen, M.-Y.; Dai, J.-J.; Guo, Q.-X.; Fu, Y. ChemSusChem 2013, 6, 1348.
(b) Chatterjee, M.; Ishizaka, T.; Kawanami, H. Green Chem. 2018, 20, 2345.
[12] Li, W.-H.; Li, C.-Y.; Li, Y.; Tang, H.-T.; Wang, H.-S.; Pan, Y.-M.; Ding, Y.-J. Chem. Commun. 2018, 54, 8446.
[13] Ogiwara, Y.; Sakurai, Y.; Hattori, H.; Sakai, N. Org. Lett. 2018, 20, 4204.
[14] Dawes, G. J. S.; Scott, E. L.; Le Nôtre, J.; Sanders, J. P. M.; Bitter, J. H. Green Chem. 2015, 17, 3231.
[15] Si, Y.-G.; Gardner, M. P.; Tarazi, F. I.; Baldessarini, R. J.; Neumeyer, J. L. J. Med. Chem. 2008, 51, 983.
[16] Cao, D.; Zeng, H.; Li, C.-J. ACS Catal. 2018, 8, 8873.
[17] Sawadjoon, S.; Lundstedt, A.; Samec, J. S. M. ACS Catal. 2013, 3, 635.
[18] Ritter, K. Synthesis 1993, 735.
[19] Pan, Y.; Holmes, C. P. Org. Lett. 2001, 3, 2769.
[20] Sajiki, H.; Mori, A.; Mizusaki, T.; Ikawa, T.; Maegawa, T.; Hirota, K. Org. Lett. 2006, 8, 987.
[21] Mori, A.; Mizusaki, T.; Ikawa, T.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Chem.-Eur. J. 2007, 13, 1432.
[22] Hupp, C. D.; Neumeyer, J. L. Tetrahedron Lett. 2010, 51, 2359.
[23] Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Chem. Front. 2014, 1, 464.
[24] Graham, T. H.; Liu, W.; Shen, D.-M. Org. Lett. 2011, 13, 6232.
[25] Matsumura, T.; Niwa, T.; Nakada, M. Tetrahedron Lett. 2012, 53, 4313.
[26] Matsumura, T.; Nakada, M. Tetrahedron Lett. 2014, 55, 1412.
[27] Ishihara, S.; Ido, A.; Monguchi, Y.; Nagase, H.; Sajiki, H. J. Hazard. Mater. 2012, 229, 15.
[28] Chelucci, G.; Baldino, S.; Ruiu, A. J. Org. Chem. 2012, 77, 9921.
[29] Kashihara, M.; Yadav, M. R.; Nakao, Y. Org. Lett. 2018, 20, 1655.
[30] Deng, G.; Chen, J.; Sun, W.; Bian, K.; Jiang, Y.; Loh, T.-P. Adv. Synth. Catal. 2018, 360, 3900.
[31] Patra, T.; Agasti, S.; Akanksha; Maiti, D. Chem. Commun. 2013, 49, 69.
[32] Patra, T.; Agasti, S.; Modak, A.; Maiti, D. Chem. Commun. 2013, 49, 8362.
[33] Enthaler, S.; Weidauer, M.; Irran, E.; Epping, J. D.; Kretschmer, R.; Someya, C. I. J. Organomet. Chem. 2013, 745, 262.
[34] Crawford, J. M.; Shelton, K. E.; Reeves, E. K.; Sadarananda, B. K.; Kalyani, D. Org. Chem. Front. 2015, 2, 726.
[35] (a) Morioka, T.; Nishizawa, A.; Furukawa, T.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2017, 139, 1416.
(b) Somerville, R. J.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 6708.
[36] Ding, K.; Shi, X.; Alotaibi, R.; Paudel, K.; Reinheimer, E. W.; Weatherly, J. J. Org. Chem. 2017, 82, 4924.
[37] Yu, R.; Chen, X.; Martin, S. F.; Wang, Z. Org. Lett. 2017, 19, 1808.
[38] Yue, H.; Guo, L.; Lee, S.-C.; Liu, X.; Rueping, M. Angew. Chem., Int. Ed. 2017, 56, 3972.
[39] Dey, A.; Sasmal, S.; Seth, K.; Lahiri, G. K.; Maiti, D. ACS Catal. 2017, 7, 433.
[40] Zhao, T.-T.; Xu, W.-H.; Zheng, Z.-J.; Xu, P.-F.; Wei, H. J. Am. Chem. Soc. 2018, 140, 586.
[41] Herrmann, J. M.; König, B. Eur. J. Org. Chem. 2013, 2013, 7017.
[42] Lipshutz, B. H.; Frieman, B. A.; Butler, T.; Kogan, V. Angew. Chem., Int. Ed. 2006, 45, 800.
[43] Álvarez-Bercedo, P.; Martin, R. J. Am. Chem. Soc. 2010, 132, 17352.
[44] Tobisu, M.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Chem. Commun. 2011, 47, 2946.
[45] Cornella, J.; Gómez-Bengoa, E.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1997.
[46] Tobisu, M.; Morioka, T.; Ohtsuki, A.; Chatani, N. Chem. Sci. 2015, 6, 3410.
[47] Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439.
[48] Sergeev, A. G.; Webb, J. D.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 20226.
[49] Li, J.; Wang, Z.-X. Chem. Commun. 2018, 54, 2138.
[50] Cao, Z.-C.; Shi, Z.-J. J. Am. Chem. Soc. 2017, 139, 6546.
[51] Lipshutz, B. H.; Tomioka, T.; Sato, K. Synlett 2001, 970.
[52] Barbero, N.; Martin, R. Org. Lett. 2012, 14, 796.
[53] Tobisu, M.; Nakamura, K.; Chatani, N. J. Am. Chem. Soc. 2014, 136. 5587.
[54] Kreis, M.; Palmelund, A.; Bunch, L.; Madsen, R. Adv. Synth. Catal. 2006, 348, 2148.
[55] Fristrup, P.; Kreis, M.; Palmelund, A.; Norrby, P.-O.; Madsen, R. J. Am. Chem. Soc. 2008, 130, 5206.
[56] Gutmann, B.; Elsner, P.; Glasnov, T.; Roberge, D. M.; Kappe, C. O. Angew. Chem., Int. Ed. 2014, 53, 11557.
[57] Monrad, R. N.; Madsen, R. J. Org. Chem. 2007, 72, 9782.
[58] Bröehmer, M. C.; Volz, N.; Bräese, S. Synlett 2009, 1383.
[59] Sun, Z.-M.; Zhang, J.; Manan, R. S.; Zhao, P. J. Am. Chem. Soc. 2010, 132, 6935.
[60] Whittaker, R. E.; Dong, G. Org. Lett. 2015, 17, 5504.
[61] Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174.
[62] Hooper, J. F.; Young, R. D.; Weller, A. S.; Willis, M. C. Chem.-Eur. J. 2013, 19, 3125.
[63] Vandekerkhove, A.; Claes, L.; De Schouwer, F.; Van Goethem, C.; Vankelecom, I. F. J.; Lagrain, B.; De Vos, D. E. ACS Sustainable Chem. Eng. 2018, 6, 9218.
[64] Chatani, N.; Tatamidani, H.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 4849.
[65] Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615.
[66] Mazziotta, A.; Madsen, R. Eur. J. Org. Chem. 2017, 2017, 5417.
[67] Nishibayashi, Y.; Shinoda, A.; Miyake, Y.; Matsuzawa, H.; Sato, M. Angew. Chem., Int. Ed. 2006, 45, 4835.
[68] Dai, X.-J.; Li, C.-J. J. Am. Chem. Soc. 2016, 138, 5433.
[69] Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756.
[70] You, T.; Wang, Z.; Chen, J.; Xia, Y. J. Org. Chem. 2017, 82, 1340.
[71] (a) Dang, H.; Cox, N.; Lalic, G. Angew. Chem., Int. Ed. 2014, 53, 752.
(b) Lei, L.; Li, C.; Mo, D. Chin. J. Org. Chem. 2019, 39, 2989(in Chinese). (雷禄, 李承璟, 莫冬亮, 有机化学, 2019, 39, 2989.)
[72] Font, M.; Quibell, J. M.; Perry, G. J. P.; Larrosa, I. Chem. Commun. 2017, 53, 5584.
[73] Gooßen, L. J.; Thiel, W. R.; Rodríguez, N.; Linder, C.; Melzer, B. Adv. Synth. Catal. 2007, 349, 2241.
[74] Goossen, L. J.; Manjolinho, F.; Khan, B. A.; Rodríguez, N. J. Org. Chem. 2009, 74, 2620.
[75] Cahiez, G.; Moyeux, A.; Gager, O.; Poizat, M. Adv. Synth. Catal. 2013, 355, 790.
[76] Li, Z.; Fu, Z.; Zhang, H.; Long, J.; Songa, Y.; Cai, H. New J. Chem. 2016, 40, 3014.
[77] Fichez, J.; Prestat, G.; Busca, P. Org. Lett. 2018, 20, 2724.
[78] Nakazawa, H.; Kamata, K.; Itazaki, M. Chem. Commun. 2005, 36, 4004.
[79] Yang, Z.; Kumar, R. K.; Liao, P.; Liu, Z.; Li, X.; Bi, X. Chem. Commun. 2016, 52, 5936.
[80] Iwai, T.; Fujihara, T.; Tsuji, Y. Chem. Commun. 2008, 46, 6215.
[81] Huang, J.-L.; Dai, X.-J.; Li, C.-J. Eur. J. Org. Chem. 2013, 2013, 6496.
[82] Yang, S.; Tang, W.; Yang, Z.; Xu, J. ACS Catal. 2018, 8, 9320.
[83] Nguyen, J. D.; Matsuura, B. S.; Stephenson, C. R. J. J. Am. Chem. Soc. 2014, 136, 1218.
[84] Lu, P.; Sanchez, C.; Cornella, J.; Larrosa, I. Org. Lett. 2009, 11, 5710.
[85] Grainger, R.; Nikmal, A.; Cornella, J.; Larrosa, I. Org. Biomol. Chem. 2012, 10, 3172.
[86] Seo, S.; Taylor, J. B.; Greaney, M. F. Chem. Commun. 2012, 48, 8270.
[87] Liao, R.-Z.; Chen, S.-L.; Siegbahn, P. E. M. ACS Catal. 2015, 5, 7350.
[88] Ren, Y.-L.; Tian, M.; Tian, X.-Z.; Wang, Q.; Shang, H.; Wang, J.; Zhang, Z. C. Catal. Commun. 2014, 52, 36.
[89] (a) Zhang, L.; Koreeda, M. J. Am. Chem. Soc. 2004, 126, 13190.
(b) Jordan, P. A.; Miller, S. J. Angew. Chem., Int. Ed. 2012, 51, 2907.
[90] García, N.; García-García, P.; Fernández-Rodríguez, M. A.; Rubio, R.; Pedrosa, M. R.; Arnáiz, F. J.; Sanz, R. Adv. Synth. Catal. 2012, 354, 321.
[91] Sousa, S. C. A.; Fernandes, T. A.; Fernandes, A. C. Eur. J. Org. Chem. 2016, 2016, 3109.
[92] (a) Dupuy, S.; Lazreg, F.; Slawin, A. M. Z.; Cazin, C. S. J.; Nolan, S. P. Chem. Commun. 2011, 47, 5455.
(b) Dupuy, S.; Nolan, S. P. Chem.-Eur. J. 2013, 19, 14034.
[93] Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741.
[94] Miura, K.; Tomita, M.; Yamada, Y.; Hosomi, A. J. Org. Chem. 2007, 72, 787.
[95] Bauer, J. O.; Chakraborty, S.; Milstein, D. ACS Catal. 2017, 7, 4462.
[96] Zou, Y.-Q.; Chakraborty, S.; Nerush, A.; Oren, D.; Diskin-Posner, Y.; Ben-David, Y.; Milstein, D. ACS Catal. 2018, 8, 8014.
[97] Moseley, J. D.; Gilday, J. P. Tetrahedron 2006, 62, 4690.
[98] Diéguez, H. R.; López, A.; Domingo, V.; Arteaga, J. F.; Dobado, J. A.; Herrador, M. M.; Quílez del Moral, J. F.; Barrero, A. F. J. Am. Chem. Soc. 2010, 132, 254.
[99] Meyer, V. J.; Niggemann, M. Chem.-Eur. J. 2012, 18, 4687.
[100] Li, P.; Ma, N.; Wang, Z.; Dai, Q.; Hu, C. J. Org. Chem. 2018, 83, 8233.
[101] Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179.
[102] Chandrasekhar, S.; Reddy, C. R.; Babu, B. N. J. Org. Chem. 2002, 67, 9080.
[103] Milne, J. E.; Storz, T.; Colyer, J. T.; Thiel, O. R.; Seran, M. D.; Larsen, R. D.; Murry, J. A. J. Org. Chem. 2011, 76, 9519.
[104] Wang, Y. P.; Liu, Y. H.; Ruan, R. S.; Wan, Y. Q.; Zhang, J. S.; Peng, H. Acta Chim. Sinica 2012, 70, 114(in Chinese). (王允圃, 刘玉环, 阮榕生, 万益琴, 张锦胜, 彭红, 化学学报, 2012, 70, 114.)
[105] Griffin, J. D.; Zeller, M. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340.
[106] Yang, W.; Gao, L.; Lu, J.; Song, Z. Chem. Commun. 2018, 54, 4834.
[107] Liu, D.; Sun, J.; Simmons, B. A.; Singh, S. ACS Sustainable Chem. Eng. 2018, 6, 7232.
[108] Zhao, X.; Zheng, X.; Yang, B.; Sheng, J.; Lu, K. Org. Biomol. Chem. 2018, 16, 1200.
[109] Fukuyama, T.; Fujita, Y.; Miyoshi, H.; Ryu, I.; Kao, S.-C.; Wu, Y.-K. Chem. Commun. 2018, 54, 5582.