可离去和/或可修饰导向基团辅助的C—H键官能化反应研究进展

doi:10.6023/cjoc201308012

摘要/Abstract

过渡金属催化的导向基团辅助的C—H键官能团化反应是当前有机化学的研究热点之一. 近年来，利用可离去和/或可修饰导向基团进行C—H键官能团化反应正受到化学家的特别关注并且发展迅速. 借助可离去或可修饰导向基团，不但能够大大扩展可利用的碳氢底物，而且对于快速构建分子多样性具有重要作用. 作者按不同杂原子（氮、氧、硫、硅等）导向基团进行分类，全面综述了近年来关于可离去和/或可修饰导向基团辅助的各种C—H键官能团化反应的研究进展及合成应用. 最后，对该领域所存在的问题和局限性进行了总结，并对今后的发展方向作了展望.

关键词: 导向基团, C—H键官能化, 过渡金属催化, 分子多样性

Transition-metal catalyzed chelation-assisted C—H bond functionalization is one of hot topics in current organic chemistry. Recently, using removable and/or modifiable directing groups for C—H bond functionalizations has being received specially attention and developed rapidly. By taking advantage of removable and/or modifiable directing groups, it not only greatly expands the scope of substrates for C—H fuctionalization, but also plays important roles in rapid construction of molecule diversity. Based on the classification according to different hetero-atom (N, O, S, and Si) donors, this review presents the state of the art in design of removable and/or modifiable directing groups for transition-metal catalyzed C—H functionalizations and their application in construction of molecule diversity. Finally, the existing problems and limitations of this field are summarized, and the outlook of the area is also prospected.

Key words: directing group, C—H bond functionalization, transition-metal catalysis, molecule diversity

引用此文

张巍, 张家慧, 刘运奎. 可离去和/或可修饰导向基团辅助的C—H键官能化反应研究进展[J]. 有机化学, 2014, 34(1): 36-53.

Zhang Wei, Zhang Jiahui, Liu Yunkui. Recent Advances in C—H Functionalizations Assisted by Removable and/or Modifiable Directing Groups[J]. Chin. J. Org. Chem., 2014, 34(1): 36-53.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Dyker, G. Handbook of C—H Transformations: Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2005.
(b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
(c) Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013.
(d) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
(e) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
(f) Ackermann, L. Chem. Commun. 2010, 4866.
(g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
(h) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
(i) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
(j) Herrmann, P.; Bach, T. Chem. Soc. Rev. 2011, 40, 2022.
(k) Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061.
(l) Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 2022.
(m) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
(n) Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864.
(o) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.
[2] For selected reviews on transition-metal-catalyzed chelation-assisted C—H activations, see: (a) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(b) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(c) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(d) Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949.
(e) Daugulis, O.; Do, H.-Q.; Shabashow, D. Acc. Chem. Rev. 2009, 42, 1074.
(f) Godula, K.; Sames, D. Science 2006, 312, 67.
(g) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
[3] Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
[4] (a) Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450.
(b) Wang, C.; Huang, Y. Synlett 2013, 145.
(c) Wang, Y.; Chen, G.; Cui, X. Chin. J. Org. Chem. 2012, 32, 2018 (in Chinese).
(王勇, 程国林, 崔秀灵, 有机化学, 2012, 32, 2018.)
[5] Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220.
[6] Chu, J.-H.; Wu, C.-C.; Chang, D.-H.; Lee, Y.-M.; Wu, M.-J. Organometallics 2013, 32, 272.
[7] Ackermann, L.; Lygin, A. V. Org. Lett. 2011, 13, 3332.
[8] Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764.
[9] Du, J.; Zhou, B.; Yang, Y.; Li, Y. Chem.-Asian J. 2013, 8, 1386.
[10] Koley, M.; Dastbaravardeh, N.; Schnürch, M.; Mihovilovic, M. D. ChemCatChem 2012, 4, 1345.
[11] Dastbaravardeh, N.; Schnürch, M.; Mihovilovic, M. D. Org. Lett. 2012, 14, 1930.
[12] Chu, J.-H.; Lin, P.-S.; Wu, M.-J. Organometallics 2010, 29, 4058.
[13] Ackermann, L.; Diers, E.; Manvar, A. Org. Lett. 2012, 14, 1154.
[14] Cong, X.; You, J.; Gao, G.; Lan, J. Chem. Commun. 2013, 662.
[15] Yu, M.; Liang, Z.; Wang, Y.; Zhang, Y. J. Org. Chem. 2011, 76, 4987.
[16] García-Rubia, A.; Fernández-Ibáňez, M. Á; Arrayás, R. G.; Carretero, J. C. Chem.-Eur. J. 2011, 17, 3567.
[17] Urones, B.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2013, 15, 1120.
[18] Rodríguez, N.; Romerco-Revilla, J. A.; Fernández-Ibáňez, M. Á.; Carretero, J. C. Chem. Sci. 2013, 4, 175.
[19] (a) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-I. J. Am. Chem. Soc. 2000, 122, 12013.
(b) Itami, K.; Nokami, T.; Yoshida, J.-I. J. Am. Chem. Soc. 2001, 123, 5600.
(c) Itami, K.; Ushiogi, Y.; Nokami, T.; Ohashi, Y.; Yoshida, J.-I. Org. Lett. 2004, 6, 3695.
(d) Kamei, T.; Itami, K.; Yoshida, J.-I. Adv. Synth. Catal. 2004, 346, 1824.
[20] (a) Huang, C.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Adv. Synth. Catal. 2011, 353, 1285.
(b) Chernyak, N.; Dudnik, A. S.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 8270.
(c) Dudnik, A. S.; Chernyak, N.; Huang, C.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 8729.
[21] (a) Ihara, H.; Koyanagi, K.; Suginome, M. Org. Lett. 2011, 13, 2662.
(b) Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502.
[22] Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237.
[23] Aihara, Y.; Chatani, N. Chem. Sci. 2013, 4, 664.
[24] Rouquet, G.; Chatani, N. Chem. Sci. 2013, 4, 2201.
[25] Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030.
[26] Huang, L.; Li, Q.; Wang, C.; Qi, C. J. Org. Chem. 2013, 78, 3030.
[27] Ryabov, A. D.; Sakodinskaya, I. K.; Yatsimirsky, A. K. J. Chem. Soc., Dalton. Trans. 1985, 2629.
[28] Wang, X.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 7520.
[29] Haffemayer, B.; Gulias, M.; Gaunt, M. J. Chem. Sci. 2011, 2, 312.
[30] (a) He, H.; Liu, W.-B.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2009, 131, 8346.
(b) Ye, K.-Y.; He, H.; Liu, W.-B.; Dai, L.-X.; Helmchen, G.; You, S.-L. J. Am. Chem. Soc. 2011, 133, 19006.
[31] Liang, Z.; Ju, L.; Kie, Y.; Huang, L.; Zhang, Y. Chem.-Eur. J. 2012, 18, 15816.
[32] Tang, C.; Jiao, N. J. Am. Chem. Soc. 2012, 134, 18924.
[33] Stuart McCallum, J.; Gasdaska, J. R.; Liebeskind, L. S.; Tremont, S. J. Tetrahedron Lett. 1989, 30, 4085.
[34] (a) Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2013, 15, 1638.
(b) Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Chem.-Eur. J. 2012, 18, 5541.
(c) Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2012, 14, 3724.
[35] Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
[36] Thirunarukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462.
[37] Dubost, E.; Fossey, C.; Cailly, T.; Rault, S.; Fabis, F. J. Org. Chem. 2011, 76, 6414.
[38] Ren, Z.; Mo, F.; Dong, G. J. Am. Chem. Soc. 2012, 134, 16991.
[39] Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Chem. Commun. 2013, 3703.
[40] (a) Liu, Y.-K.; Lou, S.-J.; Xu, D.-Q.; Xu, Z.-Y. Chem.-Eur. J. 2010, 16, 13590.
(b) Zhang, W.; Lou, S.; Liu, Y.; Xu, Z. J. Org. Chem. 2013, 78, 13590.
[41] Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931.
[42] Chen, Y.; Wang, F.; Zhen, W.; Li, X. Adv. Synth. Catal. 2013, 355, 353.
[43] Zhen, W.; Wang, F.; Zhao, M.; Du, Z.; Li, X. Angew. Chem., Int. Ed. 2012, 51, 11819.
[44] Ma, X.-T.; Tian, S.-K. Adv. Synth. Catal. 2013, 355, 337.
[45] Muralirajan, K.; Cheng, C.-H. Chem.-Eur. J. 2013, 19, 6198.
[46] Lian, Y.; Bergman, R. G.; Lavis, L. D.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 7122.
[47] Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713.
[48] Wang, C.; Chen, H.; Wang, Z.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242.
[49] Liu, B.; Fan, Y.; Gao, Y.; Sun, C.; Xu, C.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 468.
[50] (a) Li, W.; Xu, Z.; Sun, P.; Jiang, X.; Fang, M. Org. Lett. 2011, 13, 1286.
(b) Li, W.; Sun, P. J. Org. Chem. 2012, 77, 8362.
(c) Du, B.; Jiang, X.; Sun, P. J. Org. Chem. 2013, 78, 2786.
[51] (a) Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072.
(b) Dai, H.-X.; Li, G.; Zhang, X.-G.; Stepan, A. F.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 7567.
(c) Leow, D.; Li, G.; Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518.
[52] Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788.
[53] (a) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379.
(b) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
[54] (a) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
(b) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407.
[55] Wang, X. S.; Lu, Y.; Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2010, 132, 12203.
[56] Lu, Y.; Leow, D. S.; Wang, X. S.; Engle, K. M.; Yu, J. Q. Chem. Sci. 2011, 2, 967.
[57] (a) Huang, C.; Ghavtadze, N.; Godoi, B.; Gevorgyan, V. Chem.-Eur. J. 2012, 18, 9789.
(b) Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 17630.
(c) Wang, C.; Ge, H. Chem.-Eur. J. 2011, 17, 14371.
[58] (a) Li, F.; Jiang, T.; Cai, H.; Wang, G. Chin. J. Chem. 2012, 30, 2041.
(b) Meng, X.; Kim, S. Org. Lett. 2013, 15, 1910.
[59] Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211.
[60] Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159.
[61] Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
[62] (a) Giri, R.; Maugel, N. L.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510.
(b) Wang, D. H.; Mei, T. S.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 17676.
(c) Mei, T. S.; Giri, R.; Maugel, N.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 5215.
(d) Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082.
(e) Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654.
(f) Engle, K. M.; Wang, D. H.; Yu, J. Q. J. Am. Chem. Soc. 2010, 132, 14137.
(g) Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460.
(h) Cheng, X.-F.; Li, Y.; Su, Y.-M.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wnag, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236.
[63] Horino, H.; Inoue, N. J. Org. Chem. 1981, 46, 4416.
[64] Tremont, S. J.; Hayatur, R. J. Am. Chem. Soc. 1984, 106, 5759.
[65] Noele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
[66] Wang, J.-R.; Yang, C.-T.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 5449.
[67] Schimidt, B.; Elizarov, N. Chem. Commun. 2012, 4350.
[68] Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
[69] Loh, T. P.; Zhou, H.; Xu, Y. H.; Chung, W. J. Angew. Chem., Int. Ed. 2009, 48, 5355.
[70] Borgduas, N.; Lough, A. J.; Dong, V. M. Inorg. Chim. Acta 2011, 369, 247.
[71] Giri, R.; Lam, J. K.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686.
[72] Zhou, B.; Yang, Y.; Liu, S.; Li, Y. Adv. Synth. Catal. 2013, 355, 360.
[73] Yang, X.; Shan, G.; Rao, Y. Org. Lett. 2013, 15, 2334.
[74] Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
[75] Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
[76] Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
[77] (a) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577.
(b) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
[78] Gandeepan, P.; Parthasarathy, K.; Cheng, C.-H. J. Am. Chem. Soc. 2010, 132, 8569.
[79] Xiao, B.; Gong, T. J.; Xu, J.; Liu, Z. J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466.
[80] Xiao, B.; Fu, Y.; Xu, J.; Gong, T. J.; Dai, J. J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468.
[81] Sun, X.; Shan, G.; Sun, Y.; Rao, Y. Angew. Chem., Int. Ed. 2013, 52, 4440.
[82] Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
[83] Yu, M.; Xie, Y.; Xie, C.; Zhang, Y. Org. Lett. 2012, 14, 2164.
[84] Yao, J.; Yu, M.; Zhang, Y. Adv. Synth. Catal. 2012, 354, 3205.
[85] Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 7534.