钯催化C—H乙酰氧基化反应

doi:10.6023/cjoc201409022

摘要/Abstract

Pd催化的C—H官能化反应是目前有机合成方法学的一个重要研究热点. 毫无疑问, 这种温和又有选择性地转化方式广泛运用于化学各个领域. 钯催化反应在近十年内得到了很大的发展,但是对于有机化学家来说仍然是一个挑战. 综述了近十年来关于在C(sp²)—H和C(sp³)—H乙酰氧基化反应的研究进展及其应用, 并提出了今后的研究重点和发展趋势.

关键词: 钯, 催化, 乙酰氧基化

Palladium-catalyzed C—H functionalization is one of the hot topics in the field of organic synthesis methodology. Mild and selective transformation of this type will undoubtedly find widespread application across the chemistry. Even though Pd-catalyzed reaction has been deeply developed over past decades, it remains to be a huge challenge in organic chemistry. Herein, this review presents the recent progress for palladium-catalyzed C(sp²)—H and C(sp³)—H acetoxylation and their applications in the synthesis of complex molecules. Moreover, the research trend of this area is also prospected.

Key words: palladium, catalysis, acetoxylation

引用此文

陈天保, 章明. 钯催化C—H乙酰氧基化反应[J]. 有机化学, 2015, 35(4): 813-826.

Chen Tianbao, Zhang Ming. Palladium-Catalyzed C—H Acetoxylation Reations[J]. Chin. J. Org. Chem., 2015, 35(4): 813-826.

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参考文献

[1] (a) Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2011, 40, 1937.
(b) Zhang, M. Adv. Syn. Catal. 2009, 351. 2243.
(c) Zhang, M. Synthesis 2011, 3408.
(d) Zhang, M. J. Chem. Res. 2013, 10, 606.
(e) Zhang, M.; Chen, T.; Liu, Q. Heterocycles 2014, 89, 1255.
(f) Zhang, M.; Zhang, A.-Q.; Peng, Y. J. Organomet. Chem. 2013, 723, 224.
(g) Zhang, M.; Zhang, A. Appl. Organomet. Chem. 2010, 24, 751.
(h) Zhang, M.; Zhang, A. Synthesis 2012, 44, 1.
(i) Yu, M. Ph.D. Dissertation, Zhejiang University, Zhejiang, 2013 (in Chinese).
(于明, 博士论文, 浙江大学, 浙江, 2013.)
(j) Li, H.; Ding C.-H.; Xu, B.; Hou, X.-L. Acta Chim. Sinica 2014, 72, 765 (in Chinese).
(李浩, 丁昌华, 许斌, 候雪龙, 化学学报, 2014, 72, 765.;
k)Yang, J.-P.; Zhang, L.; Jin, X.-P.; Gao, H.-Q.; Fang, J.-H.; Li, R.-F.; Fang, Y.-W. Chin. J. Org. Chem. 2013, 33, 1647 (in Chinese).
(杨建平, 张莉, 金小平, 高浩其, 房江华, 李瑞丰, 方烨汶, 有机化学, 2013, 33, 1647.)
[2] (a) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104 , 3453.
(b) Zhang, B.; Guan, H.-X.; Lin, B.; Shi, B.-F. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese).
(张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.;
c) Pan, F.; Shi, Z.-J. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).
(潘菲, 施章杰, 化学学报, 2012, 70, 1679.;
d) Cai, H.-T.; Li, D.-D.; Liu, Z.; Wang G.-W. Acta Chim. Sinica 2013, 71, 717 (in Chinese).
(蔡海婷, 李单单, 刘资, 王官武, 化学学报, 2013, 71, 717.)
(e) li, D.-D.; He, C.-L.; Cai, H.-T.; Wang, G.-W. Chin. J. Org. Chem. 2013, 33, 203 (in Chinese).
(李丹丹, 何程林, 蔡海婷, 王官武, 有机化学, 2013, 33, 203.)
(f) Du, L; Cao, P.; Liao, J. Acta Chim. Sinica 2013, 71, 1239 (in Chinese).
(杜乐, 曹鹏, 廖建, 化学学报, 2013, 71, 1239.;
g) Tang, B.-X.; Fang, X.-N.; Kuang, R.-Y.; Zhou, X.-C. Chin. J. Org. Chem. 2013, 33, 319 (in Chinese).
(唐伯萧, 方小牛, 匡仁云, 周小春, 有机化学, 2013, 33, 319.;
h) Ma, Y.-Y.; Li, W.; Yu, B. Acta Chim. Sinica 2013, 71, 541 (in Chinese).
(马玉勇, 李微, 俞飚, 化学学报, 2013, 71, 541.)
[3] Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[4] Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
[5] Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 19, 4149.
[6] Richter, H.; Beckendorf, S.; Mancheno, G. Adv. Synth Catal. 2011, 353, 295.
[7] Sanford, M. S.; Desai, L. V.; Stowers, K. J. J. Am. Chem. Soc. 2008, 130, 13285.
[8] Patpi, S. R.;Sridhar, B.;Tadikamalla, P. R.;Kantevari, S. RSC Adv. 2013, 3, 10251.
[9] Wang, G.-W.; Yuan, T.-T.; Wu, X.-L. J. Org. Chem. 2008, 73, 4717.
[10] Gou, F.-R.; Wang, X.-C.; Huo, P.-F.; Bi ,H.-P.; Guan, Z.-H.; Liang, Y.-M. Org, Lett. 2009, 11, 24, 5726.
[11] Subba Reddy, B.V.; Revathi, G. A.; Srinivas, R.; Yadav, J. S. Tetrahedron Lett. 2011, 52, 5926.
[12] Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Chem. Eur. J. 2012 , 18, 5541.
[13] Cheng, X.-F.; Li, Y.; Su , Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236.
[14] Yang, M.; Jiang, X.; Shi, W.-J.; Zhu, Q.-L.; Shi, Z.-J. Org. Lett. 2013, 15, 690.
[15] Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2014, 16, 968.
[16] Yang, F.; Song, F.-J.; Li, W.; Lan, J.-b.; You, J. S. RSC Adv. 2013, 3, 9649.
[17] Gu, S.-J.; Chen, C.; Chen, W.-Z. J. Org. Chem. 2009, 74, 7203.
[18] Zheng, X.-J.; Song, B. R.; Xu, B. Eur. J. Org. Chem. 2010, 4376.
[19] Subba Reddy, B. V.; Ramesh, K.;Yadav, J. S. Synlett 2011, 22, 9.
[20] Subba Reddy, B. V.; Narasimhulu, G.; Umadevi, N.; Yadav, J. S. Synlett 2012, 23, 1364.
[21] Ren, X.-Y; Liu, J.;Yan, H.; Shi, X.-K; Yang, S.-Z; Li, J.; Huang, G.-S. Synlett 2013, 24, 95.
[22] Leng, Y.-T. Yang, F.; Zhu, W.-G.; Wu, Y.-J.; Li, X. Org. Biomol. Chem. 2011, 9, 5288
[23] Banerjee, A.; Bera, A.; Santra, S. K.; Srimanta Guin, S.; Patel, B. RSC Adv. 2014, 4, 8558.
[24] Ding, Q.-P.; Ji, H.-F.; Nie, Z.-Y.; Yang, Q.; Peng, Y.-Y. J. Organomet. Chem. 2013, 739. 33.
[25] Wang, L.; Xia, X.-D.; Guo, W.; Chen, J.-D.; Xiao, W.-J. Org. Biomol. Chem. 2011, 9, 6895
[26] Desai, L. V.; Malik, H. A.; Sanford, M. S. Org, Lett. 2006, 8, 1141.
[27] Vickers, C. J.; Mei, T. S.; Yu, J.-Q. Org. Lett. 2010, 12, 2511.
[28] Subba Reddy, B. V.; Umadevi, N.; Narasimhulu, G.; Yadav, J. S. Tetrahedron Lett. 2012, 53, 6091.
[29] Chan, L. Y.; Meng, X. J.; Kim, S. J. Org. Chem. 2013, 78, 8826.
[30] Zhang, H.; Hu, R.-B.; Zhang, X.-Y.; Lia, S.-X.; Yang, S.-D. Chem. Commun. 2014, 50, 4686.
[31] Mutule, L.; Suna, E.; Olofsson, K; Pelcman, B. J. Org. Chem. 2009, 74, 7195.
[32] Liang, Z.-J.; Zhao, J.-L.; Zhang, Y.-H. J. Org. Chem. 2009, 75, 170.
[33] Choy, P. Y.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2011, 76, 80.
[34] Liu, Q.; Li, Q.; Yi, H.; Wu, P.; Liu, J.; Lei, A. Chem. Eur. J. 2011, 17, 2353.
[35] Cook, A. K.; Emmert, M. H.; Sanford, M. S. Org. Lett. 2013, 15, 5428.
[36] Gary, J. B.; Cook, A. K.; Sanford, M. S. ACS Catal. 2013, 3, 700.
[37] Subba Reddy, B. V.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
[38] Ju, L.; Yao, J.-Z.; Wu, Z.-H.; Liu, Z.-X.; Zhang, Y.-H. J. Org. Chem. 2013, 78, 10821.
[39] Cheng, T.; Yin, W.-Y.; Zhang, Y.; Zhang, Y.-N.; Huang, Y. Org. Biomol. Chem. 2014, 12, 1405.
[40] Jiang, H.-F.; Chen, H.-J.; Wang, Z.; Liu, X.-H. Chem. Commun. 2010, 46, 7259.
[41] Zhang, J.; Khaskin, E.; Anderson, N. P.; Zavalij, P. Y.; Vedernikov, A. N. Chem. Commun. 2008, 3625.
[42] Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
[43] Neufeldt, S. R.; Sanford, M. S. Org. Lett. 2010, 12, 532.
[44] Ren, Z.; Mo, F. Y.; Dong, G. B. J. Am. Chem. Soc. 2012, 134, 16991.
[45] Wang, D.-H.; Hao, X.-S.; Wu, D.-F.; Yu, J. Q. Org. Lett. 2006, 8, 3387.
[46] Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2012, 14, 3724.
[47] Giri, R.; Liang, J.; Lei, J.-G.; Li, J. J.;Wang, D. H.; Chen, X.; Naggar, I. C.; Guo, C. Y.; Foxman, B. M.; Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 7420.