Recent Advances in the Norbornene Mediated Palladium-Catalyzed Domino-Type Catellani Reaction

doi:10.6023/cjoc201505035

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2291-2300.DOI: 10.6023/cjoc201505035 Previous Articles Next Articles

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降冰片烯促进的钯催化多米诺Catellani反应研究进展

朱辉, 叶长青, 陈知远

江西师范大学化学化工学院功能有机小分子教育部重点实验室南昌 330022

收稿日期:2015-05-25 修回日期:2015-06-23 发布日期:2015-07-08
通讯作者: 陈知远 E-mail:zchen@jxnu.edu.cn
基金资助:
国家自然科学基金(Nos. 21202065, 21462022)和江西省自然科学基金(No. 20142BAB213004)资助项目.

Recent Advances in the Norbornene Mediated Palladium-Catalyzed Domino-Type Catellani Reaction

Zhu Hui, Ye Changqing, Chen Zhiyuan

Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received:2015-05-25 Revised:2015-06-23 Published:2015-07-08
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21202065, 21462022) and the Natural Science Foundation of Jiangxi Province (No. 20142BAB213004).

Catellani reaction is a kind of domino reaction that can achieve direct functionalization of the unactivated remote aromatic C—H bond, based on the use of a palladium catalyst and norbornene. Through the selective activation of the C—H bond which located at the ortho position of C—X, and a subsequent direct cross coupling reaction in the ipso position of aryl halide, the reaction employing aryl halide as a starting material opens a way for the selective formation of many new chemical bonds, as well as multi-substituted aromatic or aza-heterocyclic derivatives in a single reaction vessel. The recent advancements that introducing different strategies to terminate the typical Catellani reaction are mainly summarized.

Key words: palladium catalyst, norbornene, C—H bond activation, Domino reaction

Cite this article

Zhu Hui, Ye Changqing, Chen Zhiyuan. Recent Advances in the Norbornene Mediated Palladium-Catalyzed Domino-Type Catellani Reaction[J]. Chin. J. Org. Chem., 2015, 35(11): 2291-2300.

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[1] Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis, John Wiley, New York, 2006.
[2] (a) Oestreich, M. The Mizoroki-Heck Reaction, Wiley, Chichester, 2009.(b) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581. (c) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
[3] Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions, Eds.: Diederich, F.; Stang, P. J.; Wiley-VCH, Weinheim, Germany, 1998; Chapter 2.
[4] For reviews: (a) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
[5] Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. 1997, 36, 119.
[6] Mitsudo, K.; Thansandote, P.; Wilhelm, T.; Mariampillai, B.; Lautens, M. Org. Lett. 2006, 8, 3939.
[7] (a) Ferraccioli, R.; Carenzi, D.; Catellani, M. Tetrahedron Lett. 2004, 45, 6903. (b) Alberico, D.; Rudolph, A.; Lautens, M. J. Org. Chem. 2007, 72, 775.
[8] Catellani, M.; Deledda, S.; Ganchegui, B.; Hénin, F.; Motti, E.; Muzart, J. J. Organomet. Chem. 2003, 687, 473.
[9] (a) Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78. (b) Motti, E.; Faccini, F.; Ferrari, I.; Catellani, M.; Ferraccioli, R. Org. Lett. 2006, 8, 3967.
[10] Lautens, M.; Piguel, S. Angew. Chem., Int. Ed. 2000, 39, 1045.
[11] Martins, A.; Marquardt, U.; Kasravi, N.; Alberico, D.; Lautens, M. J. Org. Chem. 2006, 71, 4937.
[12] Rudolph, A.; Rackelmann, N.; Turcotte-Savard, M.-O.; Lautens, M. J. Org. Chem. 2009, 74, 289.
[13] Zhang, H.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2014, 53, 10174.
[14] (a) Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680. (b) Berman, A. M.; Johnson, J. S. J. Org. Chem. 2005, 70, 364. (c) Berman, A. M.; Johnson, J. S. J. Org. Chem. 2006, 71, 219.
[15] Chen, Z.; Ye, C.; Zhu, H.; Zeng, X.; Yuan, J. Chem.-Eur. J. 2014, 20, 4237.
[16] Catellani, M.; Motti, E.; Minari, M. Chem. Commun. 2000, 157.
[17] Motti, E.; Catellani, M. J. Mol. Catal. A: Chem. 2003, 204, 115.
[18] Ye, C.; Zhu, H.; Chen, Z. J. Org. Chem. 2014, 79, 8900.
[19] Scott, M. E.; Alberico, D.; Lautens, M. Chem. Rev. 2007, 107, 174.
[20] Catellani, M.; Motti, E.; Baratta, S. Org. Lett. 2001, 3, 3611.
[21] Liu, H.; El-Salfiti, M.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 9846.
[22] (a) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148. (b) Blaszykowski, C.; Aktoudianakis, E.; Alberico, D.; Bressy, C.; Hulcoop, D. G.; Jafarpour, F.; Joushaghani, A.; Laleu, B.; Lautens, M. J. Org. Chem. 2008, 73, 1888. (c) Jafarpour, F.; Lautens, M. Org. Lett. 2006, 8, 3601. (d) Blaszykowski, C.; Aktoudianakis, E.; Bressy, C.; Alberico, D.; Lautens, M. Org. Lett. 2006, 8, 2043. (e) Laleu, B.; Lautens, M. J. Org. Chem. 2008, 73, 9164.
[23] (a) Martins, A.; Alberico, D.; Lautens, M. Org. Lett. 2006, 8, 4827. (b) Martins, A.; Lautens, M. J. Org. Chem. 2008, 73, 8705.
[24] Ferraccioli, R.; Carenzi, D.; Rombolà, O.; Catellani, M. Org. Lett. 2004, 6, 4759.
[25] Thansandote, P.; Raemy, M.; Rudolph, A.; Lautens, M. Org. Lett. 2007, 9, 5255.
[26] Thansandote, P.; Chong, E.; Feldmann, K.-O.; Lautens, M. J. Org. Chem. 2010, 75, 3495.
[27] Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 3312.
[28] Deledda, S.; Motti, E.; Catellani, M. Can. J. Chem. 2005, 83, 741.
[29] Wilhelm, T.; Lautens, M. Org. Lett. 2005, 7, 4053.
[30] Martins, A.; Lautens, M. Org. Lett. 2008, 10, 5095.
[31] (a) Jiao, L.; Bach, T. J. Am. Chem. Soc. 2011, 133, 12990. (b) Jiao, L.; Herdtweck, E.; Bach, T. J. Am. Chem. Soc. 2012, 134, 14563.
[32] Dong, Z.; Dong, G. J. Am. Chem. Soc. 2013, 135, 18350.
[33] Wang, X.-C.; Gong, W.; Fang, L.-Z.; Zhu, R.-Y.; Li, S.; Engle, K. M.; Yu, J.-Q. Nature 2015, 519, 334.
[34] Dong, Z.; Wang, J.; Dong, G. J. Am. Chem. Soc. 2015, 137, 5887.
[35] (a) Cassar, L. J. Organomet. Chem. 1975, 93, 253. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467.
[36] Negishi, E.-I.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
[37] Motti, E.; Rossetti, M.; Bocelli, G.; Catellani, M. J Organomet. Chem. 2004, 689, 3741.
[38] Gallazzi, M. C.; Hanlon, T. L.; Vitulli, G.; Porri, L. J Organomet. Chem. 1971, 33, C45.
[39] Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2003, 42, 1661.
[40] (a) Mariampillai, B.; Alberico, D.; Bidau, V.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 14436. (b) Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 15372.
[41] Zhao, Y.-B.; Mariampillai, B.; Candito, D. A.; Laleu, B.; Li, M.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 1849.
[42] Barluenga, J.; Valdes, C. Angew. Chem., Int. Ed. 2011, 50, 7486.
[43] Chen, Z.-S.; Duan, X.-H.; Wu, L.-Y.; Ali, S.; Ji, K.-G.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2011, 17, 6918.
[44] Zhou, P.-X.; Ye, Y.-Y.; Ma, J.-W.; Zheng, L.; Tang, Q.; Qiu, Y.-F.; Song, B.; Qiu, Z.-H.; Xu, P.-F.; Liang, Y.-M. J. Org. Chem. 2014, 79, 6627.
[45] Shi, H.; Babinski, D. J.; Ritter, T. J. Am. Chem. Soc. 2015, 137, 3775.
[46] Sun, F.; Gu, Z. Org. Lett. 2015, 17, 2222.

降冰片烯促进的钯催化多米诺Catellani反应研究进展

Recent Advances in the Norbornene Mediated Palladium-Catalyzed Domino-Type Catellani Reaction

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