Pd催化(杂环)芳基羧酸脱羧的偶联反应研究进展

doi:10.6023/cjoc201409029

摘要/Abstract

羧酸具有无毒、廉价易得、稳定易存储等特点, 有关过渡金属Pd催化(杂环)芳基羧酸脱羧的偶联反应在本世纪来得到了迅速发展, 大有取代传统偶联反应之势. 本文综述了Pd催化(杂环)芳基羧酸脱羧与多种底物的偶联反应, 如烯、芳基卤化物、芳烃, 三氟芳基硼酸盐等底物, 并对相关的反应机理进行了探讨.

关键词: Pd, (杂环)芳基羧酸, 脱羧, 偶联反应

Since carboxylic acids have distinguishing features of non-toxicity, low cost, ready availability and easy storage, Pd-catalyzed decarboxylative coupling reactions of (hetero)aromatic carboxylic acids have been obtained rapid development since this century, and have exhibited a tendency toward replacement of traditional coupling reactions. The coupling reactions of Pd-catalyzed decarboxylation of aromatic carboxylic acids with various substrates of olefins, aryl halides, arenes, aryltrifluoroborates and etc. are reviewed, and the relevant reaction mechanisms are discussed.

Key words: Pd, (hetero)aromatic carboxylic acid, decarboxylation, coupling reaction

引用此文

付拯江, 李兆杰, 熊起恒, 蔡琥. Pd催化(杂环)芳基羧酸脱羧的偶联反应研究进展[J]. 有机化学, 2015, 35(5): 984-996.

Fu Zhengjiang, Li Zhaojie, Xiong Qiheng, Cai Hu. Recent Progress in Pd-Catalyzed Decarboxylative Coupling Reactions of (Hetero)aromatic Carboxylic Acids[J]. Chin. J. Org. Chem., 2015, 35(5): 984-996.

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参考文献

[1] (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442. (c) McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885. (d) Zhang, Y.; Luo, S.; Zhu, C. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese). (张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.) (e) Yang, J.; Deng, M.; Yu, T. Chin. J. Org. Chem. 2013, 33, 693 (in Chinese). (杨军, 邓敏智, 于涛, 有机化学, 2013, 33, 693.) (f) Yang, M.; Pei, J.; Yan, G.; Weng, Q. Chin. J. Org. Chem. 2013, 33, 343 (in Chinese). (杨明华, 裴吉, 严国兵, 翁秋月, 有机化学, 2013, 33, 343.) (g) Xuan, S.; Wang, X.; Wang, J.; Zhao, B.; Cheng, K.; Qi, C. Chin. J. Org. Chem. 2014, 34, 1743 (in Chinese). (宣赏赐, 王晓丹, 王建伟, 赵保丽, 程凯, 齐陈泽, 有机化学, 2014, 34, 1743.) (h) Ni, C.; Shen, A.; Cao, Y.; Ye, X. Chin. J. Org. Chem. 2014, 34, 278 (in Chinese). (倪晨, 沈安, 曹育才, 叶晓峰, 有机化学, 2014, 34, 278.)
[2] (a) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. (b) Wang, N.-X. Chin. J. Org. Chem. 2011, 31, 1319 (in Chinese). (王乃兴, 有机化学, 2011, 31, 1319.).
[3] Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653.
[4] (a) 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. (b) Wang, D.-H.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 17676.
[5] Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
[6] Wu, Z.; Chen, S.; Hu, C.; Li, Z.; Xiang, H.; Zhou, X. ChemCatChem 2013, 5, 2839.
[7] Ng, F.-N.; Zhou, Z.; Yu, W.-Y. Chem. Eur. J. 2014, 20, 4474.
[8] (a) Gooβen, L. J.; Rodr?′guez, N.; Gooβen, K. Angew. Chem., Int. Ed. 2008, 47, 3100. (b) Feng, C.; Liu, S.; Peng, S.; Yi, B.; Deng, G. Prog. Chem. 2010, 22, 1403 (in Chinese). (冯超, 刘赛文, 彭圣明, 易兵, 邓国军, 化学进展, 2010, 22, 1403.) (c) Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030. (d) Shang, R.; Liu, L. Sci. China Chem. 2011, 54, 1670. (e) Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653. (f) Dai, J.; Wang, G.; Xu, X.; Xu, H. Chin. J. Org. Chem. 2013, 33, 2460 (in Chinese). (戴建军, 王光祖, 徐小岚, 许华建, 有机化学, 2013, 33, 2460.)
[9] (a) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (b) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75. (c) Xiao, Y.; Fu, B.; Qin, Z.-H. Chin. J. Org. Chem. 2005, 25, 751 (in Chinese). (肖玉梅, 傅滨, 覃兆海, 有机化学, 2005, 25, 751.) (d) Li, Z.; Fu, Y.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2005, 25, 1508 (in Chinese). (李哲, 傅尧, 刘磊, 郭庆祥, 有机化学, 2005, 25, 1508.) (e) Wang, D.; Zhang, X.-D.; Liang, Y.; L. J.-H. Chin. J. Org. Chem. 2006, 26, 19 (in Chinese). (王德平, 张旭东, 梁云, 李金恒, 有机化学, 2006, 26, 19.) (f) Li, W.; Zhao, D.; X. X.; Ma, Q.; Cheng, M. Chin. J. Org. Chem. 2011, 31, 784 (in Chinese). (李文燕, 赵冬梅, 熊绪琼, 马倩倩, 程卯生, 有机化学, 2011, 31, 784.) (g) Liu, N.; Liu, C.; Jin, Z. Chin. J. Org. Chem. 2012, 32, 860 (in Chinese). (刘宁, 刘春, 金子林, 有机化学, 2012, 32, 860.) (h) Cheng, Y.; Sun, L. Chin. J. Org. Chem. 2013, 33, 877 (in Chinese). (成宜娟, 孙丽萍, 有机化学, 2013, 33, 877.) (i) Lei, A.; Zhang, H. In C—H and C—X Bond Functionalization: Transition Metal Mediation, Ed.: Ribas, X., RSC Catalysis Series, London, 2013, pp. 310~327.
[10] (a) Nilsson, M. Acta Chem. Scand. 1966, 20, 423. (b) Björklund, C.; Nilsson, M. Acta Chem. Scand 1968, 22, 2585.
[11] Cairncross, A; Roland, J. R,; Henderson, R. M.; Sheppard, W. A. J. Am. Chem. Soc. 1970, 92, 3187.
[12] Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250.
[13] Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
[14] Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350.
[15] (a) Gooßen, L. J.; Thiel, W. R.; Rodríguez, N.; Linder, C.; Melzer, B. Adv. Synth. Catal. 2007, 349, 2241. (b) Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem., Int. Ed. 2009, 48, 792. (c) Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 9350. (d) Zhao, D.; Gao, C.; Su, X.; He, Y.; You, J.; Xue, Y. Chem. Commun. 2010,46, 9049. (e) Ranjit, S.; Duan, Z.; Zhang, P.; Liu, X. Org. Lett. 2010, 12, 4134. (f) Hu, J.; Zhao, N.; Yang, B.; Wang, G.; Guo, L.-N.; Liang, Y.-M.; Yang, S. D. Chem. Eur. J. 2011, 17, 5516. (g) Yang, H.; Sun, P.; Zhu, Y.; Yan, H.; Lu, L.; Qu, X.; Li, T.; Mao, J. Chem. Commun. 2012, 48, 2368. (h) Yu, L.; Li, P.; Wang, L. Chem. Commun. 2013, 49, 2368. (i) Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 155. (j) Song, Q.; Feng, Q.; Zhou, M. Org. Lett. 2013, 15, 5990. (k) He, Z.; Zhang, R.; Hu, M.; Li, L.; Ni, C.; Hu, J. Chem. Sci. 2013, 4, 3478. (l) Jiang, Q.; Xu, B.; Jia, J.; Zhao, A.; Zhao, Y.-R.; Li, Y.-Y.; He, N.-N.; Guo, C.-C. J. Org. Chem. 2014, 79, 7372.
[16] (a) Goossen, L. J.; Linder, C.; Rodriguez, N.; Lange, P. P.; Fromm, A. Chem. Commun. 2009, 7173. (b) Cornella, J.; Sanchez, C.; Banawa, D.; Larrosa, I. Chem. Commun. 2009, 7176. (c) Luo, Y.; Pan, X.; Wu, J. Tetrahedron Lett. 2010, 51, 6646. (d) Wang, Z.; Zhu, L.; Yin, F.; Su, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 4258. (e) Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401. (f) Seo, S.; Slater, M.; Greaney, M. F. Org. Lett. 2012, 14, 2650. (g) Wang, H.; Guo, L.-N.; Duan, X.-H. Adv. Synth. Catal. 2013, 355, 2222. (h) Zhao, W.-M.; Chen, X.-L.; Yuan, J.-W.; Qu, L.-B.; Duan, L.-K.; Zhao, Y.-F. Chem. Commun. 2014, 50, 2018. (i) Hu, F.; Shao, X.; Zhu, D.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105. (j) Wang, P.-F.; Wang, X.-Q.; Dai, J.-J.; Feng, Y.-S.; Xu, H.-J. Org. Lett. 2014, 16, 4586.
[17] (a) Sun, Z.-M.; Zhang, J.; Zhao, P. Org. Lett. 2010, 12, 992. (b) Sun, Z.-M.; Zhao, P. Angew. Chem., Int. Ed. 2009, 48, 6726. (c) Wang, J.; Liu, B.; Zhao, H.; Wang, J. Organometallics 2012, 31, 8598. (d) Pan, F.; Lei, Z.-Q.; Wang, H.; Li, H.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2013, 52, 2063. (e) Zhang, L.; Qiu, R.; Xue, X.; Pan, Y.; Xu, C.; Wang, D.; Wang, X.; Xu, L.; Li, H. Chem. Commun. 2014, 50, 12385.
[18] (a) Cornella, J.; Rosillo-Lopez, M.; Larrosa, I. Adv. Synth. Catal. 2011, 353, 1359. (b) Dupuy, S.; Nolan, S. P. Chem. Eur. J. 2013, 19, 14034.
[19] (a) Bi, H.-P.; Chen, W.-W.; Liang, Y.-M.; Li, C.-J. Org. Lett. 2009, 11, 3246. (b) Patra, T.; Deb, A.; Manna, S.; Sharma, U.; Maiti, D. Eur. J. Org. Chem. 2013, 5247. (c) Yang, H.; Yan, H.; Sun, P.; Zhu, Y.; Lu, L.; Liu, D.; Rong, G.; Mao, J. Green Chem. 2013,15, 976. (d) Zhao, J.; Zhou, W.; Han, J.; Li, G.; Pan, Y. Tetrahedron Lett. 2013, 54, 6507.
[20] Chen, L.; Li, H.; Yu, F.; Wang, L. Chem. Commun. 2014, 50, 14866.
[21] (a) Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. 1997, 36, 155. (b) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147. (c) Arroyave, F. A.; Reynolds, J. R. Org. Lett. 2010, 12, 1328. (d) Lange, P. P.; Goossen, L. J.; Podmore, P.; Underwood, T.; Sciammetta, N. Chem. Commun. 2011, 3628.
[22] Tanaka, D.; Myers, A. G. Org. Lett. 2004, 6, 433.
[23] Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323.
[24] Zhang, S.-L.; Fu, Y.; Shang, R.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638.
[25] Xue, L.; Su, W.; Lin, Z. Dalton Trans. 2010, 39, 9815.
[26] (a) Hu, P.; Kan, J.; Su, W.; Hong, M. Org. Lett. 2009, 11, 2341. (b) Fu, Z.; Huang, S.; Su, W.; Hong, M. Org. Lett. 2010, 12, 4992.
[27] Fardost, A.; Lindh, J.; Sjçberg, P. J. R.; Larhed, M. Adv. Synth. Catal. 2014, 356, 870.
[28] Zhao, Y.; Zhang, Y.; Wang, J.; Li, H.; Wu, L.; Liu, Z. Synlett 2010, 2352.
[29] Gigant, N.; Chausset-Boissarie, L.; Gillaizeau, I. Org. Lett. 2013, 15, 816.
[30] Xiang, S.; Cai, S.; Zeng, J.; Liu, X.-W. Org. Lett. 2011, 13, 4608.
[31] Huang, L.; Qi, J.; Wu, X.; Huang, K.; Jiang, H. Org. Lett. 2013, 15, 2330.
[32] Fu, Z.; Huang, S.; Kan, J.; Su, W.; Hong, M. Dalton Trans. 2010, 39, 11317.
[33] Zhang, M.; Zhou, J.; Kan, J.; Wang, M.; Su, W.; Hong, M. Chem. Commun. 2010, 46, 5455.
[34] Zhou, J.; Wu, G.; Zhang, M.; Jie, X.; Su, W. Chem. Eur. J. 2012, 18, 8032.
[35] Goossen, L. J.; Zimmermann, B.; Knauber, T. Beilstein J. Org. Chem. 2010, 6, 43.
[36] Wang, J.; Cui, Z.; Zhang, Y.; Li, H.; Wu, L.-M.; Liu, Z. Org. Biomol. Chem. 2011, 9, 663.
[37] (a) Fu, G. C. Acc. Chem. Res. 2008,41, 1555. (b) Johansson Seechurn,C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
[38] Bilodeau, F.; Brochu, M.-C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550.
[39] Nakano, M.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1851.
[40] Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2009, 351, 2683.
[41] Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M. Chem. Eur. J. 2009, 15, 3674.
[42] Shang, R.; Xu,. Q.; Jiang, Y.-Y.; Wang, Y.; Liu, L. Org. Lett. 2010, 12, 1000.
[43] He, R.-T.; Wang, J.-F.; Wang, H.-F.; Ren, Z.-G.; Lang, J.-P. Dalton Trans. 2014, 43, 9786.
[44] Shen, Z.; Ni, Z.; Mo, S.; Wang, J.; Zhu, Y. Chem. Eur. J. 2012, 18, 4859.
[45] Goossen, L. J.; Rodriguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824.
[46] Goossen, L. J.; Zimmermann, B.; Knauber, T. Angew. Chem., Int. Ed. 2008, 47, 7103.
[47] Goossen, L. J.; Rodríguez, N.; Linder, C. J. Am. Chem. Soc. 2008, 130, 15248.
[48] Goossen, L. J.; Rodríguez, N.; Lange, P. P.; Linder, C. Angew. Chem., Int. Ed. 2010, 49, 1111.
[49] Song, B.; Knauber, T.; Goossen, L. J. Angew. Chem., Int. Ed. 2013, 53, 2954.
[50] Fromm, A.; van Wüllen, C.; Hackenberger, D.; Goossen, L. J. J. Am. Chem. Soc. 2014, 136, 10007.
[51] Li, L.; Zou, D.; Leng, F.; Sun, C.; Li, J.; Wu, Y.; Wu, Y. Chem. Commun. 2013, 49, 312.
[52] Haley, C. K.; Gilmore, C. D.; Stoltz, B. M. Tetrahedron 2013, 69, 5732.
[53] Rouchet, J.-B.; Schneider, C.; Spitz, C.; Lefèvre, J.; Dupas, G.; Fruit, C.; Hoarau, C. Chem. Eur. J. 2014, 20, 3610.
[54] Lu, P.; Sanchez, C.; Cornella, J.; Larrosa, I. Org. Lett. 2009, 11, 5710.
[55] Becht, J.-M.; Catala, C.; Le Drian, C.; Wagner, A. Org. Lett. 2007, 9, 1781.
[56] Becht, J.-M.; Le Drian, C. Org. Lett. 2008, 10, 3161.
[57] Bielawski, M.; Olofsson, B. Chem. Commun. 2007, 2521.
[58] Wang, Z.; Ding, Q.; He, X.; Wu, J. Tetrahedron 2009, 65, 4635.
[59] Goossen, L. J.; Lange, P. P.; Rodríguez, N.; Linder, C. Chem. Eur. J. 2010, 16, 3906.
[60] Zhang, F.; Greaney, M. F. Org. Lett. 2010, 12, 4745.
[61] Messaoudi, S. ; Brion, J.-D. ; Alami, M. Org. Lett. 2012, 14, 1496.
[62] Voutchkova, A.; Coplin, A.; Leadbeater, N. E.; Crabtree, R. H. Chem. Commun. 2008, 6312.
[63] Wang, C.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 4194.
[64] Xie, K.; Yang, Z.; Zhou, X.; Li, X.; Wang, S.; Tan, Z.; An, X.; Guo, C.-C. Org. Lett. 2010, 12, 1564.
[65] Zhao, H.; Wei, Y.; Xu, J.; Kan, J.; Su, W.; Hong, M. J. Org. Chem. 2011, 76, 882.
[66] Luo, H.-Q.; Dong, W.; Loh, T.-P. Tetrahedron Lett. 2013, 54, 2833.
[67] Hu, P.; Zhang, M.; Jie, X.; Su, W. Angew. Chem., Int. Ed. 2012, 51, 227.
[68] Zhou, J.; Hu, P.; Zhang, M.; Huang, S.; Wang, M.; Su, W. Chem. Eur. J. 2010, 16, 5876.
[69] Cornella, J.; Lu, P.; Larrosa, I. Org. Lett. 2009, 11, 5506.
[70] Zhang, F.; Greaney, M. F. Angew. Chem., Int. Ed. 2010, 49, 2768.
[71] Hu, P.; Shang, Y.; Su, W. Angew. Chem., Int. Ed. 2012, 51, 5945.
[72] Xie, K.; Wang, S.; Yang, Z.; Liu, J.; Wang, A.; Li, X.; Tan, Z.; Guo, C.-C.; Deng, W. Eur. J. Org. Chem. 2011, 5787.
[73] Cornella, J.; Lahlali, H.; Larrosa, I. Chem. Commun. 2010, 46, 8276.
[74] Dai, J.-J.; Liu, J.-H.; Luo, D.-F.; Liu, L. Chem. Commun. 2011, 47, 677.
[75] Mino, T.; Yoshizawa, E.; Watanabe, K.; Abe, T.; Hirai, K.; Sa-kamoto, M. Tetrahedron Lett. 2014, 55, 3184.
[76] De Martino, G.; Edler, M. C.; La Regina, G.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947.
[77] Duan, Z.; Ranjit, S.; Zhang, P.; Liu, X. Chem. Eur. J. 2009, 15, 3666.
[78] Becht, J.-M.; Drian, C. L. J. Org. Chem. 2011, 76, 6327.
[79] Fu, Z.; Li, Z.; Xiong, Q.; Cai, H. Eur. J. Org. Chem. 2014, 7798.
[80] (a) Chu, L.; Yue, X.; Qing, F.-L. Org. Lett. 2011, 13, 1644. (b) Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1964, 76, 221. (c) Nace, H.; Monagle, J. J. Org. Chem. 1959, 24, 1792. (d) Kenney, W. J.; Walsh, J. A.; Davenport, D. A. J. Am. Chem. Soc. 1961, 83, 4019.
[81] Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006.
[82] Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 2337.
[83] Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodriguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043.
[84] Lindh, J.; Sjörberg, P. J.; Larhed, M. Angew. Chem., Int. Ed. 2010, 49, 7733.
[85] (a) Zhou, C. X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302 . (b) Zhou, C. X.; Larock, R. C. J. Org. Chem. 2006, 71, 3551.
[86] (a) Li, Y.; Wu, Y.; Li, G.-S.; Wang, X.-S. Adv. Synth. Catal. 2014, 356, 1412. (b) Janin, Y. L. Chem. Rev. 2012, 112, 3924. (c) Grushin, V. V. Acc. Chem. Res. 2010, 43, 160. (d) Podgoršek, A.; Zupan, M.; Iskra, J. Angew. Chem., Int. Ed. 2009, 48, 8424.
[87] Luo, Y.; Pan, X.; Wu, J. Tetrahedron Lett. 2010, 51, 6646.
[88] Peng, X.; Shao, X.-F.; Liu, Z.-Q. Tetrahedron Lett. 2013, 54, 3079.