Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (02): 203-223.DOI: 10.6023/cjoc201209022 Previous Articles Next Articles
Reviews
李丹丹, 何程林, 蔡海婷, 王官武
收稿日期:2012-09-17
修回日期:2012-10-19
发布日期:2012-10-26
通讯作者:
王官武
E-mail:gwang@ustc.edu.cn
基金资助:国家自然科学基金(No. 21132007)和安徽省高校省级自然科学研究重大(No. KJ2010ZD05)资助项目.
Li Dandan, He Chenglin, Cai Haiting, Wang Guanwu
Received:2012-09-17
Revised:2012-10-19
Published:2012-10-26
Supported by:Project supported by the National Natural Science Foundation of China (No. 21132007) and the Key Project of Science and Technology of the Department of Education, Anhui Province (No. KJ2010ZD05).
Share
Li Dandan, He Chenglin, Cai Haiting, Wang Guanwu. Palladium-Catalyzed Group-Directed sp2-C—H Functionalization[J]. Chin. J. Org. Chem., 2013, 33(02): 203-223.
| [1] (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320. (b) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581. [2] (a) Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866. (b) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 36, 3437. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Suzuki, A. Chem. Commun. 2005, 38, 4759. [3] (a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636. (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (c) Milstein, D., Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992. [4] (a) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918. (b) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507. [5] (a) Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729. (b) Negishi, E.; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596. [6] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467. [7] (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609. [8] Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330. [9] Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047. [10] Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234. [11] Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904. [12] Yu, W. Y.; Sit, W. N.; Zhou, Z.; Chan, A. S. C. Org. Lett. 2009, 11, 3174. [13] Chen, X.; Li, J. J.; Hao, X. S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78. [14] Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634. [15] Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882. [16] Zhang, Y.; Feng, J.; Li, C.-J. J. Am. Chem. Soc. 2008, 130, 2900. [17] Yu, W.-Y.; Sit, W. N.; Lai, K.-M.; Zhou, Z.; Chan. A. S. C. J. Am. Chem. Soc. 2008, 130, 3304. [18] Jia, X.; Zhang, S.; Wang, W.; Luo, F.; Cheng, J. Org. Lett. 2009, 11, 3120. [19] Baslé, O.; Bidange, J.; Shuai, Q.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 1145. [20] Li, M.; Ge, H. Org. Lett. 2010, 12, 3464. [21] Peng, X.; Zhu, Y.; Ramirez, T. A.; Zhao, B.; Shi, Y. Org. Lett. 2011, 13, 5244. [22] Jia, X.; Yang, D.; Zhang, S.; Cheng, J. Org. Lett. 2009, 11, 4716. [23] Kim, J.; Chang, S. J. Am. Chem. Soc. 2010, 132, 10272. [24] Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648. [25] (a) Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878. (b) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682. (c) Ball, N. D.; Gary, J. B.; Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577. [26] Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300. [27] Kalberer, E. W.; Whitfield, S. L.; Sanford, M. S. J. Mol. Catal., A 2006, 251, 108. [28] Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439. [29] (a) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790. (b) Racowski, J. M.; Dick, A. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 10974. [30] (a) Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285. (b) Stowers, K. J.; Sanford, M. S. Org. Lett. 2009, 11, 4584. [31] Kim, S. H.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 5863. [32] Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048. [33] Dick, A. R.; Remy, M. S.; Kampf, J. W.; Sanford, M. S. Organometallics 2007, 26, 1365. [34] Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523. [35] Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134. [36] Arnold, P. L.; Sanford, M. S.; Pearson, S. M. J. Am. Chem. Soc. 2009, 131, 13912. [37] Zhao, X.; Dimitrijevi?, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466. [38] Horino, H.; Inoue, N. J. Org. Chem. 1981, 46, 4416. [39] Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759. [40] Boele, 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. [41] Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156. [42] Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046. [43] Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066. [44] Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554. [45] Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115. [46] Brasche, G.; García-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207. [47] Zhou, H.; Xu, Y.-H.; Chung, W.-J.; Loh, T.-P.; Angew. Chem., Int. Ed. 2009, 48, 5355. [48] Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066. [49] Houlden, C. E.; Hutchby, M.; Bailey, C. D.; Ford, J. G.; Tyler, S. N. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. Angew. Chem., Int. Ed. 2009, 48, 1830. [50] (a) Nishikata, T.; Abela, A. R.; Lipshutz, B. H. Angew. Chem., Int. Ed. 2010, 49, 781. (b) Nishikata, T.; Abela, A. R.; Huang, S.; Lipshutz, B. H. J. Am. Chem. Soc. 2010, 132, 4978. [51] Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250. [52] Wang, G.-W.; Yuan, T.-T.; Wu, X.-L. J. Org. Chem. 2008, 73, 7417. [53] Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560. [54] Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996. [55] Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605. [56] Ng, K.-H.; Chan, A. S. C.; Yu, W.-Y. J. Am. Chem. Soc. 2010, 132, 12862. [57] Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416. [58] Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211. [59] Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510. [60] Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879. [61] Wang, D.-H.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 17676. [62] Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082. [63] Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 6097. [64] Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 6169. [65] Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460. [66] Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315. [67] Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654. [68] Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 5215. [69] Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655. [70] Shabashov, D.; Daugulis, O. Org. Lett. 2006, 8, 4947. [71] Shabashov, D.; Maldonado, J. R. M.; Daugulis, O. J. Org. Chem. 2008, 73, 7818. [72] Li, J.-J; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452. [73] Wasa, M.; Worrell, B. T.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 1275. [74] Yeung, C. S.; Zhao, X.; Borduas, N.; Dong, V. M. Chem. Sci. 2010, 1, 331. [75] Zhu, C.; Falck, J. R. Org. Lett. 2011, 13, 1214. [76] Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476. [77] Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380. [78] Karthikeyan, J.; Cheng, C.-H. Angew. Chem., Int. Ed. 2011, 50, 9880. [79] Li, D.-D.; Yuan, T.-T.; Wang, G.-W. Chem. Commun. 2011, 47, 12789. [80] Wasa, M.; Engle, K. M.; Yu, J-.Q. J. Am. Chem. Soc. 2010, 132 , 3680. [81] Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916. [82] Wrigglesworth, J. W.; Cox, B.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. Org. Lett. 2011, 13, 5326. [83] Li, D.-D.; Yuan, T.-T.; Wang, G.-W. J. Org. Chem. 2012, 77, 3341. [84] Zhong, H.; Yang, D.; Wang, S.; Huang, J. Chem. Commun. 2012, 48, 3236. [85] Péron, F.; Fossey, C.; Cailly, T.; Fabis, F. Org. Lett. 2012, 14, 1827. [86] (a) Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931. (b) Inamoto, K.; Saito, T.; Hiroyo, K.; Doi, T. Synlett 2008, 3157. [87] Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058. [88] Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452. [89] Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806. [90] Yoo, E. J.; Ma, S.; Mei, T.-S.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652. [91] Wang, X.; Leow, D.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 13864. [92] Chan, K. S. L.; Wasa, M.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 9081. [93] Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 134. [94] Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740. [95] Kawamura, Y.; Satoh, T.; Miura, M.; Nomura, M. Chem. Lett. 1997, 1103. [96] Lu, Y.; Leow, D.; Wang, X.; Engle, K. M.; Yu, J.-Q. Chem. Sci. 2011, 2, 967. [97] Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203. [98] Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250. [99] Campbell, A. N.; White, P. B.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 15116. [100] Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406. [101] Gandeepan, P.; Parthasarathy, K.; Cheng, C.-H. J. Am. Chem. Soc. 2010, 132, 8569. [102] Xiao, B.; Fu, Y.; Xu, J.; Gong, T.-J.; Dai, J.-J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468. [103] Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466. [104] Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856. [105] Sezen, B.; Franz, R.; Sames, D. J. Am. Chem. Soc. 2002, 124, 13372. [106] Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154. [107] Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391. [108] Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414. [109] Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965. [110] Zhao, Y.; Chen, G. Org. Lett. 2011, 13, 4850. [111] Ano, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2012, 14, 354. [112] He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3. [113] Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7. [114] Zhang, S.-Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313. [115] Zhao, Y.; He, G.; Nack, W. A.; Chen, G. Org. Lett. 2012, 14, 2948. [116] He, G.; Lu, C.; Zhao, Y.; Nack, W. A.; Chen, G. Org. Lett. 2012, 14, 2944. [117] Zhu, B.; Wang, G.-W. Org. Lett. 2009, 11, 4334. [118] Chuang, S.-C.; Rajeshkumar, V.; Cheng, C.-A.; Deng, J.-C.; Wang, G.-W. J. Org. Chem. 2011, 76, 1599. [119] Li, F.; Liu, T.-X.; Wang, G.-W. Org. Lett. 2012, 14, 2176. [120] Su, Y.-T.; Wang, Y.-L.; Wang, G.-W. Chem. Commun. 2012, 48, 8132. |
| [1] | Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447. |
| [2] | Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348. |
| [3] | Yanshuo Zhu, Hongyan Wang, Penghua Shu, Ke'na Zhang, Qilin Wang. Recent Advances on Alkoxy Radicals-Mediated C(sp3)—H Bond Functionalization via 1,5-Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 1-17. |
| [4] | Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136. |
| [5] | Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627. |
| [6] | Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681. |
| [7] | Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527. |
| [8] | Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052. |
| [9] | Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225. |
| [10] | Linsheng Bai, Peng Hong, Anguo Ying. Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1241-1270. |
| [11] | Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044. |
| [12] | Yannian Pan, Xiao Qin, Chengkai Yuan, Yi Lu. Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 924-948. |
| [13] | Hongyu Hou, Yuanyuan Cheng, Bin Chen, Chenho Tung, Lizhu Wu. α-Acylation of Olefins via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1012-1022. |
| [14] | Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621. |
| [15] | Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704. |
| Viewed | ||||||
|
Full text |
|
|||||
|
Abstract |
|
|||||
