氧化偶联反应的最新研究进展

doi:10.6023/cjoc201411028

有机化学 ›› 2015, Vol. 35 ›› Issue (4): 743-759.DOI: 10.6023/cjoc201411028 上一篇下一篇

研究专题

氧化偶联反应的最新研究进展

张剑^a, 陆庆全^a, 刘超^a, 雷爱文^a,b

a 武汉大学化学与分子科学学院高等研究院武汉 430027;
b 江西师范大学国家单糖化学合成工程技术研究中心南昌 330022

收稿日期:2014-11-14 修回日期:2015-01-24 发布日期:2015-01-28
通讯作者: 雷爱文 E-mail:aiwenlei@whu.edu.cn
基金资助:
科技部973计划(Nos. 2012CB725302, 2011CB808600)、国家自然科学基金(Nos. 21390400, 21272180, 21302148)、高等学校博士学科点专项科研基金资助(No. 20120141130002)、教育部长江学者和创新团队发展计划(No. IRT1030)、国家科学技术部基金(No. 2012YQ120060)、高等学校学科创新引智计划(111项目)资助项目.

Recent Advances in Oxidative Coupling Reactions

Zhang Jian^a, Lu Qingquan^a, Liu Chao^a, Lei Aiwen^a,b

a College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072;
b National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022

Received:2014-11-14 Revised:2015-01-24 Published:2015-01-28
Supported by:
Project supported by the 973 Program (Nos. 2012CB725302, 2011CB808600), the National Natural Science Foundation of China (Nos. 21390400, 21272180, and 21302148), and the Research Fund for the Doctoral Program of Higher Education of China (No. 20120141130002), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1030), the Ministry of Science and Technology of China (No. 2012YQ120060) and the Program of Introducing Talents of Discipline to Universities of China (111 Program).

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摘要/Abstract

近年来, 过渡金属催化的氧化偶联反应已成为有机合成化学中构建碳—碳键以及各类碳—杂键的重要方法. 主要综述了我们研究小组在氧化偶联领域, 尤其是第三代氧化偶联反应方面所取得的研究进展, 介绍了各类反应的特点、优势及在合成中的应用.

关键词: 氧化偶联, 氧化羰基化, 氧化酯化, 亲核试剂

Recently, transition-metal-catalyzed oxidative coupling reactions have emerged as the most important and attractive methods to construct carbon-carbon bond and carbon-heteroatom bonds in organic synthetic chemistry. This review mainly summarizes our research progress in the area of oxidative coupling and their versatility, application in organic synthesis, especially for the third generation of oxidative coupling.

Key words: oxidative coupling, oxidative carbonylation, oxidative esterification, nuclephiles

引用此文

张剑, 陆庆全, 刘超, 雷爱文. 氧化偶联反应的最新研究进展[J]. 有机化学, 2015, 35(4): 743-759.

Zhang Jian, Lu Qingquan, Liu Chao, Lei Aiwen. Recent Advances in Oxidative Coupling Reactions[J]. Chin. J. Org. Chem., 2015, 35(4): 743-759.

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参考文献

[1] Negishi, E.-I.; de Meijere, A. Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley-Interscience, New York, 2002.
[2] (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
(b) Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866.
(c) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
(d) Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729.
(e) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
(f) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 1995, 34, 1348.
[3] (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(b) Liu, Q.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2011, 50, 10788.
(c) Shi, W.; Liu, C.; Lei, A. Chem. Soc. Rev. 2011, 40, 2761.
(d) Liu, C.; Jin, L. Synlett 2010, 2527.
[4] Lipshutz, B. H.; Siegmann, K.; Garcia, E.; Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276
[5] Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048.
[6] Jin, L.; Zhao, Y.; Zhu, L.; Zhang, H.; Lei, A. Adv. Synth. Catal. 2009, 351, 630.
[7] Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 2439
[8] Zhao, Y.; Jin, L.; Li, P.; Lei, A. J. Am. Chem. Soc. 2008, 130, 9429.
[9] (a) Luh, T.; Leung, M.; Wong, K. Chem. Rev. 2000, 100, 3187.
(b) Woell, J. B.; Fergusson, S. B.; Alper, H. J. Org. Chem. 1985, 50, 2134.
[10] Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674.
[11] Liu, Q.; Li, G.; He, J.; Liu, J.; Li, P.; Lei, A. Angew. Chem., Int. Ed. 2010, 49, 3371.
[12] Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2003, 44, 1541.
[13] (a) Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898.
(b) Guan, Z.; Ren, Z.; Spinella, S. M.; Yu, S.; Liang, Y.; Zhang, X. J. Am. Chem. Soc. 2008, 131, 729.
(c) Giri, R.; Yu, J. J. Am. Chem. Soc. 2008, 130, 14082.
[14] (a) Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898.
(b) Guan, Z. H.; Ren, Z. H.; Spinella, S. M.; Yu, S. C.; Liang, Y. M.; Zhang, X. M. J. Am. Chem. Soc. 2009, 131, 729.
(c) Giri, R.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 14082.
(d) Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
(e) Zhao, Y.; Jin, L.; Li, P.; Lei, A. J. Am. Chem. Soc. 2008, 130, 9429.
[15] (a) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642.
(b) Altenhoff, G.; Wuertz, S.; Glorius, F. Tetrahedron Lett. 2006, 47, 2925.
(c) Cahiez, G.; Gager, O.; Buendia, J. Angew. Chem., Int. Ed. 2010, 49, 1278.
[16] Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132, 4101.
[17] Izawa, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2004, 77, 2033.
[18] Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. J. Chem. Res., Synop. 1993, 434.
[19] Fuchita, Y.; Utsunomiya, Y.; Yasutake, M. J. Chem. Soc., Dalton Trans. 2001, 2330.
[20] Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300
[21] (a) Kamata, K.; Yamaguchi, S.; Kotani, M.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407.
(b) Eglinton, G.; Galbraith, A. R. Chem. Ind. 1956, 737.
(c) Hay, A. S. J. Org. Chem. 1960, 25, 1275.
(d) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
(e) Ranu, B. C.; Banerjee, S. Lett. Org. Chem. 2006, 3, 607.
(f) Jiang, H.-F.; Tang, J.-Y.; Wang, A. Z.; Deng, G.-H.; Yang, S.-R. Synthesis 2006, 1155.
(g) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Gayathri, K. U.; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493.
(h) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
(i) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
[22] (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
(b) Glaser, C. Ann. Chem. Pharm. 1870, 154, 137.
(c) Yang, F.; Cui, X.; Li, Y.-N.; Zhang, J.; Ren, G.-R.; Wu, Y. Tetrahedron 2007, 63, 1963.
(d) Shi, M.; Qian, H.-X. Appl. Organomet. Chem. 2006, 20, 771.
(e) Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523.
(f) Qian, M.; Negishi, E. Org. Process Res. Dev. 2003, 7, 412.
(g) Lei, A.; Srivastava, M.; Zhang, X. J. Org. Chem. 2002, 67, 1969.
(h) Chalifoux, W. A.; Ferguson, M. J.; Tykwinski, R. R. Eur. J. Org. Chem. 2007, 1001.
(i) Yan, J.; Lin, F.; Yang, Z. Synthesis 2007, 1301.
[23] (a) Shun, A. L. K. S.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2006, 45, 1034.
(b) Haley, M. M.; Tykwinski, R. R. Carbon-Rich Compounds: From Molecules to Materials, Wiley-VCH, Weinheim, 2006.
(c) Diederich, F.; Stang, P. J.; Tykwinski, R. R. Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005.
[24] (a) Kim, S.; Kim, S.; Lee, T.; Ko, H.; Kim, D. Org. Lett. 2004, 6, 3601.
(b) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 4075.
(c) Montierth, J. M.; DeMario, D. R.; Kurth, M. J.; Schore, N. E. Tetrahedron 1998, 54, 11741.
(d) Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763.
[25] Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2008, 11, 709.
[26] (a) Matsumoto, F.; Chujo, Y. Pure Appl. Chem. 2006, 78, 1407.
(b) Butler, P.; Gallagher, J. F.; Manning, A. R.; Mueller-Bunz, H.; McAdam, C. J.; Simpson, J.; Robinson, B. H. J. Organomet. Chem. 2005, 690, 4545.
(c) McAdam, C. J.; Manning, A. R.; Robinson, B. H.; Simpson, J. Inorg. Chim. Acta 2005, 358, 1673.
(d) Gallagher, J. F.; Butler, P.; Hudson, R. D. A.; Manning, A. R. J. Chem. Soc., Dalton Trans. 2002, 75.
(e) Butler, P.; Gallagher, J. F.; Manning, A. R. Inorg. Chem. Commun. 1998, 1, 343.
(f) Onitsuka, K.; Tao, X. Q.; Sonogashira, K. Bull. Chem. Soc. Jpn. 1994, 67, 2611.
(g) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021.
(h) Miyano, S.; Izumi, Y.; Hashimoto, H. J. Chem. Soc., Chem. Commun. 1978, 446.
[27] (a) Lanci, M. P.; Brinkley, D. W.; Stone, K. L.; Smirnov, V. V.; Roth, J. P. Angew. Chem., Int. Ed. 2005, 44, 7273.
(b) Kieber-Emmons, M. T.; Riordan, C. G. Acc. Chem. Res. 2007, 40, 618.
[28] (a) Smith, E. H.; Whittall, J. Organometallics 1994, 13, 5169.
(b) Klein, H. F.; Beck-Hemetsberger, H.; Reitzel, L.; Rodenhaeuser, B.; Cordier, G. Chem. Ber. 1989, 122, 43.
[29] (a) Kamata, K.; Yamaguchi, S.; Kotani, M.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407.
(b) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
[30] Liu, Q.; Li, G.; He, J.; Liu, J.; Li, P.; Lei, A. Angew. Chem., Int. Ed. 2010, 49, 3371.
[31] (a) Belmont, P. In Silver in Organic Chemistry, Ed.: Harmata, M., John Wiley & Sons Inc., Hoboken, NJ, 2010, Chapter 5, pp. 143～165.
(b) Alvarez-Corral, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. Chem. Rev. 2008, 108, 3174.
(c) Weibel, J. M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149.
[32] (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
(b) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
(c) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
(d) Keay, B. A. Chem. Soc. Rev. 1999, 28, 209.
(e) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850.
(f) Balme, G.; Bouyssi, D.; Monteiro, N. Heterocycles 2007, 73, 87.
[33] Tang, P.; Ritter, T. Tetrahedron 2011, 67, 4449.
[34] Viterisi, A.; Orsini, A.; Weibel, J.-M.; Pale, P. Tetrahedron Lett. 2006, 47, 2779.
[35] (a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
(b) Snider, B. B. Chem. Rev. 1996, 96, 339.
(c) Alagoz, O.; Yilmaz, M.; Tarik Pekel, A. Synth. Commun. 2006, 36, 1005.
(d) Lee, Y. R.; Byun, M. W.; Kim, B. S. Bull. Korean Chem. Soc. 1998, 19, 1080.
(e) Liu, W.; Jiang, H.; Zhang, M.; Qi, C. J. Org. Chem. 2010, 75, 966.
(f) Yan, R.; Huang, J.; Luo, J.; Wen, P.; Huang, G.; Liang, Y. Synlett 2010, 1071.
(g) Sivan, A.; Deepthi, A.; Nandialath, V. Synthesis 2011, 2466.
[36] Katritzky, A. R. Comprehensive Heterocyclic Chemistry III, Elsevier, Amsterdam, New York, 2008.
[37] (a) Katritzky, A. R.; Xu, Y.-J.; Tu, H. J. Org. Chem. 2003, 68, 4935.
(b) Langer, S. Z.; Arbilla, S.; Benavides, J.; Scatton, B. Adv. Biochem. Psychopharmacol. 1990, 46, 61.
(c) Carminati, G. M. Farmaco, Ed. Prat. 1978, 33, 68.
(d) Allen, J.; Parent, G.; Tizot, A. J. Labelled Compd. Radiopharm. 1986, 23, 807.
[38] (a) Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
(b) Yadav, J. S.; Reddy, B. V. S. Y.; Rao, G.; Srinivas, M.; Narsaiah, A. V. Tetrahedron Lett. 2007, 48, 7717.
(c) Bakherad, M.; Nasr-Isfahani, H.; Keivanloo, A.; Doostmohammadi, N. Tetrahedron Lett. 2008, 49, 3819.
(d) Adib, M.; Mohamadi, A.; Sheikhi, E.; Ansari, S.; Bijanzadeh, H. R. Synlett. 2010, 1606.
[39] He, C.; Hao, J.; Xu, H.; Mo, Y.; Liu, H.; Han, J.; Lei, A. Chem. Commun. 2012, 48, 11073.
[40] He, C.; Guo, S.; Ke, J.; Hao, J.; Xu, H.; Chen, H.; Lei, A. J. Am. Chem. Soc. 2012, 134, 5766.
[41] Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080.
[42] (a) Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318.
(b) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
[43] (a) Zhao, Y.; Jin, L.; Li, P.; Lei, A. J. Am. Chem. Soc. 2008, 130, 9429.
(b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
(c) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(d) Lu, W.; Yamaoka, Y.; Taniguchi, Y.; Kitamura, T.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1999, 580, 290.
(e) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
(f) Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082.
(g) Guan, Z.-H.; Ren, Z.-H.; Spinella, S. M.; Yu, S.; Liang, Y.-M.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 729.
(h) Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898.
(i) Yu. L. M.; Xu, Q. H.; Cai, M. Z. Chin. J. Org. Chem. 2008, 28, 256 (in Chinese).
(余腊妹, 许秋华, 蔡明中, 有机化学, 2008, 28, 256.)
[44] (a) Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
(b) Ohashi, S.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2005, 486.
(c) Haffemayer, B.; Gulias, M.; Gaunt, M. J. Chem. Sci. 2011, 2, 312.
[45] (a) Bew, S. P. Compr. Org. Funct. Group Transform. II 2005, 5, 19.
(b) Goossen, L. J.; Rodriguez, N.; Goossen, K. Angew. Chem. 2008, 120, 3144; Angew. Chem., Int. Ed. 2008, 47, 3100.
(c) Itahara, T. Chem. Lett. 1982, 1151.
(d) Itahara, T. Chem. Lett. 1983, 127.
[46] (a) Okamoto, N.; Miwa, Y.; Minami, H.; Takeda, K.; Yanada, R. Angew. Chem. 2009, 121, 9873; Angew. Chem. Int. Ed. 2009, 48, 9693.
(b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(c) Wolfe, J. P.; Thomas, J. S. Curr. Org. Chem. 2005, 9, 625.
(d) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673.
[47] Zhang, H.; Liu, D.; Chen, C.; Liu, C.; Lei, A. Chem. Eur. J. 2011, 17, 9581.
[48] (a) Bew, S. P. Compr. Org. Funct. Group Transform. II 2005, 5, 19.
(b) Goossen, L. J.; Rodriguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
[49] (a) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.
(b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(c) Wolfe, J. P.; Thomas, J. S. Curr. Org. Chem. 2005, 9, 625.
(d) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
(e) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
(f) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673.
[50] (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
(b) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(c) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(d) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
[51] Liu, Q.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2011, 50, 10788.
[52] (a) Peres, V.; Nagem, T. J.; de Oliveira, F. F. Phytochemistry 2000, 55, 683.
(b) Pinto, M. M. M.; Sousa, M. E.; Nascimento, M. S. J. Curr. Med. Chem. 2005, 12, 2517.
(c) Vieira, L. M. M.; Kijjoa, A. Curr. Med. Chem. 2005, 12, 2413.
(d) Riscoe, M.; Kelly, J. X.; Winter, R. Curr. Med. Chem. 2005, 12, 2539.
(e) El-Seedi, H. R.; El-Ghorab, D. M. H.; El-Barbary, M. A.; Zayed, M. F.; Goeransson, U.; Larsson, S.; Verpoorte, R. Curr. Med. Chem. 2009, 16, 2581.
(f) Saleem, M.; Nazir, M.; Ali, M. S.; Hussain, H.; Lee, Y. S.; Riaz, N.; Jabbar, A. Nat. Prod. Rep. 2010, 27, 238.
[53] Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 4273.
[54] Zhang, H.; Shi, R.; Gan, P.; Liu, C.; Ding, A.; Wang, Q.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5204.
[55] Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129.
[56] (a) Izawa, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2004, 77, 2033.
(b) Hu, Y.; Liu, J.; Lu, Z.; Luo, X.; Zhang, H.; Lan, Y.; Lei, A. J. Am. Chem. Soc. 2010, 132, 3153.
[57] Otera, J. Esterification: Methods, Reactions, and Applications, Wiley-VCH, Weinheim, 2003.
[58] (a) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
(b) Brennfuhrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114.
[59] (a) Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd ed., Wiley-VCH, New York, 1999.
(b) Li, Q. L.; Gu, C. Z.; Yin, H.; Zhang, Y. Chin. J. Org. Chem. 2005, 25, 1416 (in Chinese).
(李前荣, 顾承志, 尹浩, 张毅, 有机化学, 2005, 25, 1416.)
[60] (a) Ekoue-Kovi, K.; Wolf, C. Chem. Eur. J. 2008, 14, 6302.
(b) Yoo, W.-J.; Li, C.-J. Tetrahedron Lett. 2007, 48, 1033.
(c) Yoo, W.-J.; Li, C.-J. J. Org. Chem. 2006, 71, 6266.
(d) Xu, B.; Liu, X.; Haubrich, J.; Friend, C. M. Nat. Chem. 2010, 2, 61.
(e) Wu, X.-F.; Darcel, C. Eur. J. Org. Chem. 2009, 1144.
[61] (a) Xu, B.; Liu, X.; Haubrich, J.; Madix, R. J.; Friend, C. M. Angew. Chem., Int. Ed. 2009, 48, 4206.
(b) Oliveira, R. L.; Kiyohara, P. K.; Rossi, L. M. Green Chem. 2009, 11, 1366.
(c) Miyamura, H.; Yasukawa, T.; Kobayashi, S. Green Chem. 2010, 12, 776.
(d) Owston, N. A.; Parker, A. J.; Williams, J. M. J. Chem. Commun. 2008, 624.
(e) Zeng, T.; Song, G.; Li, C.-J. Chem. Commun. 2009, 6249.
(f) Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Milstein, D. Dalton Trans. 2007, 107.
(g) Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840.
[62] Liu, C.; Wang, J.; Meng, L.; Deng, Y.; Li, Y.; Lei, A. Angew. Chem., Int. Ed. 2011, 50, 5144.
[63] Luo, X.; Zhang, H.; Duan, H.; Liu, Q.; Zhu, L.; Zhang, T.; Lei, A. Org. Lett. 2007, 9, 4571.
[64] (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
(b) Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774.
(c) Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227.
(d) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400.
(e) Kroutil, W.; Mang, H.; Edegger, K.; Faber, K. Adv. Synth. Catal. 2004, 346, 125.
(f) Mallat, T.; Baiker, A. Chem. Rev. 2004, 104, 3037.
[65] (a) Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.
(b) Otera, J. Esterification: Methods, Reactions, and Applications, Wiley-VCH, Weinheim, 2003.
[66] Liu, C.; Tang, S.; Zheng, L.; Liu, D.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5662.
[67] Liu, C.; Tang, S.; Lei, A. Chem. Commun. 2013, 49, 1324.
[68] Muzart, J. Tetrahedron 2003, 59, 5789.
[69] Marquard, S. L.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 7119.
[70] (a) Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787.
(b) Zuideveld, M. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Klusener, P. A. A.; Stil, H. A.; Roobeek, C. F. J. Am. Chem. Soc. 1998, 120, 7977.
[71] (a) Massari, S.; Daelemans, D.; Barreca, M. L.; Knezevich, A.; Sabatini, S.; Cecchetti, V.; Marcello, A.; Pannecouque, C.; Tabarrini, O. J. Med. Chem. 2010, 53, 641.
(b) Black, L. A.; Cowart, M. D.; Gfesser, G. A.; Wakefield, B. D.; Altenbach, R. J.; Liu, H.; Zhao, C.; Hsieh, G. C. WO 2009085945, 2009 [Chem. Abstr. 2009, 151, 123980].
(c) Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwell, A. D. J. Med. Chem. 2008, 51, 5135.
[72] (a) Moghaddam, F. M.; Boeini, H. Z. Synlett 2005, 1612.
(b) Bose, D. S.; Idrees, M. Tetrahedron Lett. 2007, 48, 669.
(c) Bose, D. S.; Idrees, M. J. Org. Chem. 2006, 71, 8261.
[73] (a) Vera, M. D.; Pelletier, J. C. J. Comb. Chem. 2007, 9, 569.
(b) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
(c) Benedi, C.; Bravo, F.; Uriz, P.; Fernandez, E.; Claver, C.; Castillon, S. Tetrahedron Lett. 2003, 44, 6073.
[74] Wang, H.; Wang, L.; Shang, J.; Li, X.; Wang, H.; Gui, J.; Lei, A. Chem. Commun. 2012, 48, 76.
[75] (a) Pozgan, F.; Dixneuf, P. H. Adv. Synth. Catal. 2009, 351, 1737.
(b) Tsai, A. S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6316.
(c) Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926.
[76] Yi, H.; Liu, Q.; Liu, J.; Zeng, Z.; Yang, Y.; Lei, A. ChemSusChem 2012, 5, 2143.
[77] (a) Baba, H.; Moriyama, K.; Togo, H. Tetrahedron Lett. 2011, 52, 4303.
(b) Kumar, V.; Sharma, A.; Sharma, M.; Sharma, U. K.; Sinha, A. K. Tetrahedron 2007, 63, 9718.
(c) Feng, J.; Liang, S.; Chen, S.-Y.; Zhang, J.; Fu, S.-S.; Yu, X.-Q. Adv. Synth. Catal. 2012, 354, 1287.
[78] Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
[79] (a) Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 6505.
(b) Borduas, N.; Powell, D. A. J. Org. Chem. 2008, 73, 7822.
(c) Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817.
(d) Correia, C. A.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 1446.
(e) Liu, X.; Zhang, Y.; Wang, L.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 6207.
(f) Wang, Z.; Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2008, 10, 1863.
(g) Fan, R.; Li, W.; Pu, D.; Zhang, L. Org. Lett. 2009, 11, 1425.
[80] Liu, L.; Floreancig, P. E. Org. Lett. 2010, 12, 4686.

氧化偶联反应的最新研究进展

Recent Advances in Oxidative Coupling Reactions

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