Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 877-890.DOI: 10.6023/cjoc201210013 Previous Articles Next Articles
Reviews
成宜娟, 孙丽萍
收稿日期:2012-10-17
修回日期:2013-01-20
发布日期:2013-01-25
通讯作者:
孙丽萍,chsunlp@yahoo.com.cn
E-mail:chsunlp@yahoo.com.cn
基金资助:国家自然科学基金(No. 21172265)和江苏省高校“青蓝工程”资助项目.
Cheng Yijuan, Sun Liping
Received:2012-10-17
Revised:2013-01-20
Published:2013-01-25
Supported by:Project supported by the National Natural Science Foundation of China (No. 21172265) and the “Qinglan Project” of Jiangsu Province.
Share
Cheng Yijuan, Sun Liping. Research Progress towards Copper-Catalyzed Coupling Reactions for C—N Bonds and C—O Bonds[J]. Chin. J. Org. Chem., 2013, 33(05): 877-890.
| [1] (a) Liu, A.-S.; Wang, X.-G.; Ou, X.-M.; Liu, S.-D.; Mo, H.-B.; Liu, X.-P.; Wang, T.-J.; He, H.-J.; Hu, L.; Huang, M.-Z.; Liu, Z.-J.; Yao, J.-R. Chin. J. Org. Chem. 2008, 28, 1772 (in Chinese). (柳爱平, 王晓光, 欧晓明, 刘曙东, 莫洪波, 刘兴平, 王婷瑾, 何海军, 胡礼, 黄明智, 刘钊杰, 姚建仁, 有机化学, 2008, 28, 1772.)(b) Zhang, J.; Xiao, G.-M. Chin. J. Petrochem. Technol. 2011, 40, 579 (in Chinese). (张进, 肖国民, 石油化工, 2011, 40, 579.) [2] (a) Dooleweerdt, K.; Fors, B. P.; Buchwald, S. L. Org. Lett. 2010, 12, 2350. (b) Swapna, K.; Kumar, A. V.; Reddy, P.; Rao, K. R. J. Org. Chem. 2009, 74, 7514. (c) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892. [3] (a) Mann, G.; Incarvito, C.; Rheigold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (b) Jammi, S.; Sakthivel, S.; Rout, L.; Mukherjee, T.; Mandal, S.; Mitra, R.; Saha, P.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 1971. [4] (a) Kuns, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400. (c) Raru, B. C.; Dey, R.; Chatterjee, T.; Ahammed, S. ChemSusChem 2012, 5, 22 [5] U1lmann, F.; Bielecki, J. Chem. Ber. 1901, 34, 2174. [6] Ullmann, F. Ber 1904. 37, 853. [7] (a) Goldberg, I. Chem. Ber 1906, 39, 1691. (b) Alvarado, P. L.; Avendano, C.; Menendez, J. C. J. Org. Chem. 1996, 61, 5865. (c) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933. (d) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2002, 43, 3091. (e) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381. [8] Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150 (in Chinese). (邓维, 刘磊, 郭庆祥, 有机化学, 2004, 24, 150.) [9] Ma, D.-W.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450. [10] Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. [11] (a) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096. (b) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954. [12] Xu, H.-J.; Man, Q.-S.; Lin, Y.-C.; Li, Y.-Y.; Feng, Y.-S. Chin. J. Org. Chem. 2010, 30, 9 (in Chinese).(许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010, 30, 9.) [13] Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13. [14] Wang, Y.-F.; Zeng, J.-H.; Cui, X.-R. Chin. J. Org. Chem. 2010, 30, 181 (in Chinese).(王晔峰, 曾京辉, 崔晓瑞, 有机化学, 2010, 30, 181.) [15] Liao, Q.; Xi, C.-J. Chin. J. Org. Chem. 2012, 32, 986 (in Chinese). (廖骞, 席婵娟, 有机化学, Chin. J. Org. Chem. 2012, 32, 986.) [16] Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64, 670. [17] (a) Gujadhur, R. K.; Venkataraman, D. J. Org. Lett. 2001, 3, 4315. (b) Gujadhur, R.; Venkataraman, D.; Kintigh, J. T. Tetrahedron Lett. 2001, 42, 4791. [18] Zhang, Y.; Yang, X.-Y.; Yao, Q.-Z.; Ma, D.-W. Org. Lett. 2012, 14, 3056. [19] Jiang, L.-Q.; Lu, X.; Zhang, H.; Jiang, Y.-W.; Ma, D.-W. J. Org. Chem. 2009, 74, 4542. [20] Yu, H.-Z.; Fu, Y.; Bai, X.-Y.; Guo, Q.-X. Prog. Chem. 2010, 22, 557. [21] Meng, F.; Wang, C.-X.; Xie, J.-W.; Zhu, X.-H.; Wan, Y.-Q. Appl. Organomet. Chem. 2011, 25, 341. [22] Kim, S.; Kim, D.; Park, J. Adv. Synth. Catal. 2009, 351, 2573. [23] Klapars, A.; Antilla, J. C.; Huang, X.-H.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. [24] Racine, E.; Monnier, F.; Vors, J. P.; Taillefer, F. Org. Lett. 2011, 13, 2818. [25] Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78. [26] Jones, G.. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205. [27] Chernick, E. T.; Ahrens, M. J.; Scheidt, K. A.; Wasielewski, M. R. J. Org. Chem. 2005, 70, 1486. [28] Lv, X.; Bao, W.-L. J. Org. Chem. 2007, 72, 3863. [29] Daly, S.; Haddow, M. F.; Orpen, A. G.; Rolls, G. T. A.; Wass, D. F.; Wingad, R. L. Organometallics 2008, 27, 3196. [30] Haldon, E.; Alvarez, E.; Nicasio, M. C.; Perez, P. J. Organometallics 2009, 28, 3815. [31] Zhang, Z.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2008, 10, 3005. [32] Salva, M. C.; Nguyen, B. L.; Cuevas, J.; Pennypacker, K. R.; Antilla, J. C. Org. Lett. 2010, 12, 1316. [33] Hammond, H.; Schmitt, M.; Bihel, F.; Antheaume, C.; Bourguignon, J. J. J. Org. Chem. 2012, 77, 417. [34] Xing, H.; Zhang, Y.; Lai, Y.-S.; Jiang, Y.-W.; Ma, D.-W. J. Org. Chem. 2012, 77, 5449. [35] Serrano, C. M.; Looper, R. E. Org. Lett. 2011, 13, 5000. [36] (a) Chen, Y.; Xie, X. A.; Ma, D.-W. J. Org. Chem. 2007, 72, 9329. (b) Chen, Y.; Wang, Y.-J.; Sun, Z.-M.; Ma. D.-W. Org. Lett. 2008, 10, 625. [37] Coste, A.; Toumi, M.; Wright, K.; Razafimahaleo, V.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 3841. [38] Zou, B.-L.; Yuan, Q.-L.; Ma, D.-W. Org. Lett. 2007, 9, 4291. [39] Diao, X.-Q.; Wang, Y.-J.; Jiang, Y.-W.; Ma, D.-W. J. Org. Chem. 2009, 74, 7974. [40] Zhong, Q.-F.; Sun, L.-P. Tetrahedron 2010, 66, 5107. [41] Yang, D.; Fu, H.; Hu, L.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 7841. [42] Lv, X.; Bao, W.-L. J. Org. Chem. 2009, 74, 5618. [43] Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. J. Org. Chem. 2011, 76, 716. [44] Wu, Z.-Q.; Huang, Q.; Zhou, X.-G.; Yu, L.-T.; Li, Z.-K.; Wu, D. Eur. J. Org. Chem. 2011, 5242. [45] (a) Wang, B.; Lu, B.; Jiang, Y.-W.; Zhang, Y.-H.; Ma, D.-W. Org. Lett. 2008, 10, 2761. (b) Yuan, Q.-L.; Ma, D.-W. J. Org. Chem. 2008, 73, 5159. (c) Xu, L.-T.; Jiang, Y.-W.; Ma, D.-W. Org. Lett. 2012, 14, 1150. [46] Minatti, A.; Buchwald, S. L. Org. Lett. 2008, 10, 2721. [47] Li, Z.; Sun, H.; Jiang, H.; Liu, H. Org. Lett. 2008, 10, 3263. [48] Gao, M.-S.; Liu, X.-J.; Wang, X.-Y.; Cai, Q.; Ding, K. Chin. J. Chem. 2011, 29, 1199. [49] Diao, X.-Q.; Xu, L.-T.; Zhu, W.; Jiang, Y.-W.; Wang, X.-Y.; Guo, Y.-L.; Ma, D.-W. Org. Lett. 2011, 13, 6422. [50] Kavala, V.; Janreddy, D.; Raihan, M.; Kuo, C. W.; Ramesh, C.; Yao, C.-F. Adv. Synth. Catal. 2012, 11～12, 2229. [51] (a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941. (b) Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657. (c) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578. (d) Zhu, L.; Guo, P.; Li, G.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535. [52] Teo, Y. C.; Yong, F. F.; Lim, G. S. Tetrahedron Lett. 2011, 52, 7171. [53] Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943. [54] Reddy, V. P.; Kumar, A. V.; Rao, K. R. Tetrahedron Lett. 2011, 52, 777. [55] Babu, S. G.; Karvembu, R. Ind. Eng. Chem. Res. 2011, 50, 9594. [56] Reddy, K. H. V.; Ramesh, G. S. K.; Karnakar, K.; Nageswar, Y. V. D Tetrahedron Lett. 2012, 53, 3061. [57] Ranu, B. C.; Dey, R.; Chatterjee, T.; Ahammed, S. ChemSusChem 2012, 5, 22. [58] Dodonova, J.; Skardziute, L.; Kazlauskas, K.; Jursenas, S.; Tumkevicius, S. Tetrahedron 2012, 68, 329. [59] Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667. [60] Pan, X.-H.; Cai, Q.; Ma, D.-W. Org. Lett. 2004, 6, 1809. [61] (a) Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151. (b) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170. [62] (a) Yuan, X.; Xu, X.; Zhou, X.; Yuan, J.; Mai, L.; Li, Y. Org. Chem. 2007, 72, 1510. (b) Zhou, X.; Zhang, H.; Yuan, J.; Mai, L.; Li, Y. Tetrahedron Lett. 2007, 28, 7236. [63] Hodgkinson, R. C.; Schulz, J.; Willis, M. C. Org. Biomol. Chem. 2009, 7, 432. [64] Liao, Q.; Zhang, L.-Y.; Li, S.-T.; Xi, C. Org. Lett. 2011, 13, 228. [65] Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109. [66] Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539. [67] (a) Ma, D.-W.; Cai, Q. Org. Lett. 2003, 5, 3799. (b) Cai, Q.; He, G.; Ma, D.-W. J. Org. Chem. 2006, 71, 5268. [68] Sperotto, E.; Klink, G. P. M.; Vries, J. G.; Koten, G. Tetrahedron 2010, 66, 9009. [69] Maiti, D.; Buchwald, S. L. J. Org. Chem. 2010, 75, 1791. [70] Wan, J.-P.; Wang, C.-P.; Liu, Y.-Y. Org. Biomol. Chem. 2011, 9, 6481. [71] Yong, F. F.; Teo, Y. C.; Yan, Y. K.; Chua, G. L. Synlett 2012, 101. [72] Qian, C.-W.; Zong, Q.-S.; Fang, D. Chin. J. Chem. 2012, 30, 199. [73] Zhang, R.-Z.; Liu, J.-M.; Wang, S.-F.; Niu, J.-Z.; Xia, C.-G.; Sun, W. ChemCatChem 2011, 3, 146. [74] Ling, P.-X.; Li, D.; Wang, X.-Y. J. Mol. Catal. A: Chem. 2012, 357, 112. [75] Chen, J.-X.; Wang, X.-Y.; Zheng, X.-W.; Ding, J.-C.; Liu, M.-C.; Wu, H.-Y. Tetrahedron 2012, 68, 8905. [76] Qu, X.-M.; Li, T.-Y.; Zhu, Y.; Sun, P.; Yang, H.-L.; Mao, J.-C. Org. Biomol. Chem. 2011, 9, 5043. [77] Altman, R. A.; Shafir, A.; Choi, A.; Lichtor, P. A.; Buchwald, S. L. J. Org. Chem. 2008, 73, 284. [78] Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 9, 5978. [79] Wang, M.; Yuan, B.-Z.; Ma, T.-M.; Jiang, H.-F.; Li, Y.-W. RSC Adv. 2012, 2, 5528. [80] Yang, K.; Li, Z.; Wang, Z.-Y.; Yao, Z.-Y.; Jiang, S. Org. Lett. 2011, 13, 4340. [81] Khusnutdinov, R. I.; Bayguzina, A. R.; Gimaletdinova, L. I.; Dzhemilev, U. M. Russ. J. Org. Chem. 2012, 48, 1191. [82] Fang, Y.; Li, C. J. Org. Chem. 2006, 71, 6427. [83] Li, Q.-L.; Liu, Q.-L.; Ge, Z.-Y.; Zhu, Y.-M. Helv. Chim. Acta 2011, 94, 1304. [84] Evindar, G.; Batey, R. A. J. Org. Chem. 2006. 71, 1802. [85] (a) Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411. (b) Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272. [86] Xu, D.; Xu, X.- F.; Liu, Z.-L.; Sun, L.-P.; You, Q.-D. Synlett 2009, 1172. [87] Lu, B.; Wang, B.; Zhang, Y.-H.; Ma, D.-W. J. Org. Chem. 2007, 72, 5337. [88] Jaseer, E. A.; Prasad, D. J. C.; Sekar, G. Tetrahedron 2010, 66, 2077. [89] Wang, R.-P.; Mo, S.; Lu, Y.-Z.; Shen, Z.-M. Adv. Synth. Catal. 2011, 353, 713. [90] Thasana, N.; Worayuthakarn, R.; Kradanrat, P.; Hohn, E.; Young, L.; Ruchirawat, S. J. Org. Chem. 2007, 72, 9379. [91] Albanese, D.; Landini, D.; Lupi, V.; Penso, M.; Scaletti. D. J. Mol. Catal. A: Chem. 2008, 288, 28. [92] Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462. [93] Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978. [94] Toumi, M.; Couty, F.; Evano, G. J. Org. Chem. 2007, 72, 9003. [95] Kabir, M. S.; Lorenz, M.; Namjoshi, O. A.; Cook, J. M. Org. Lett. 2010, 12, 464. [96] Winternheimer, D. J.; Merlic, C. A. Org. Lett. 2010, 12, 2508. [97] Wan, J.-P.; Wang, C.-P.; Liu, Y.-Y. Appl. Organomet. Chem. 2012, 26, 445. [98] Limberger, J.; Leal, B. C.; Back, D. F.; Dupont, J.; Monteiro, A. L. Adv. Synth. Catal. 2012, 354, 1429. [99] Kumar, G. S.; Maheswari, C. U.; Kumar, R. A.; Kantam, M. L.; Reddy, K. R. Angew. Chem., Int. Ed. 2011, 50, 11748. [100] Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652. |
| [1] | Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40. |
| [2] | Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613. |
| [3] | Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119. |
| [4] | Chunyang Liu, Yan Li, Qian Zhang. Copper-Catalyzed Allylic C(sp3)—H Sulfonylation of Cyclic Olefins [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1091-1101. |
| [5] | Zujia Lu, Jian Qin, Jinting Wu, Wenli Cao, Baolong Kuang, Jianguo Zhang. Advances in the Synthesis of Energetic Compounds Based on 1,2,3-Triazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 526-554. |
| [6] | Fen Wang, Lanting Wang, Gang Wang, Cheng Qian, Yingxia Zhou, Xin Zheng. Research Progress of Fluorescent Organic Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4147-4156. |
| [7] | Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035. |
| [8] | Can Yong, Yun Li, Tao Bi, Guofeng Chen, Dongxia Zheng, Zhouyu Wang, Yuanyuan Zhang. Research Progress on the Synthesis and Activity of D-Galactose Derived Small Galectin Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1307-1325. |
| [9] | Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964. |
| [10] | Yuqing He, Lin Chen, Ruili He, Keli Zhong, Lijun Tang. Research Progress of Fluorescence Probes Constructed by Cyclodextrin Derivatives and Inclusion Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 785-795. |
| [11] | Yamin Sun, Xiyong Li, Jinwei Yuan, Jialin Yu, Shuainan Liu. CuI-Catalyzed Regioselective Synthesis of 3-Arylcoumarins with Arylamines under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 631-640. |
| [12] | Gucheng Yuan, Qinghua Bian, Min Wang, Jiangchun Zhong. Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2571-2586. |
| [13] | Mingyang Sun, Kun Xu, Bingbing Guo, Chengchu Zeng. Copper-Catalyzed Vicinal C(sp2)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2302-2309. |
| [14] | Changxing Ji, Guangxia Wang, Hua Wang. Progress in Metal-Organic Supramolecular System Based on Subcomponent Self-Assembly [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2261-2279. |
| [15] | Boshi Han, Zheng Shi, Huihong He, Xinghua Zhang. Study on the Copper-Catalyzed Selective Allylation of Aryl (or Alkyl) Halides [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 695-701. |
| Viewed | ||||||
|
Full text |
|
|||||
|
Abstract |
|
|||||
