手性磷酸控制的不对称碳氢芳基化反应合成平面手性二茂铁化合物

doi:10.6023/cjoc201602032

摘要/Abstract

报道了钯催化的分子内不对称C-H键芳基化反应.以简单易得的二茂铁羰基化合物为底物,Pd(CH₃CN)₄(OTf)₂为催化剂,使用手性磷酸作为唯一手性源,Buchwald类型联苯单膦配体,甲苯作溶剂,100℃进行反应,得到一系列二茂铁化合物,ee值最高可达83%.该反应为合成平面手性二茂铁化合物提供了一种新途径.

关键词: 钯催化, C-H键活化, 不对称催化, 手性磷酸, 二茂铁

Transition-metal-catalyzed direct activation reactions of unreactive C-H bond has been extensively developed in recent years. Although numerous synthetic methods have been reported to build diverse complex compounds, enantioselective C-H activation has not been paid much attention probably because of the absence of suitable ligands to control the stereoselectivity in the C-H activation reaction. Herein, a Pd(0)-catalyzed enantioselective synthesis of planar chiral ferrocenes was described, and chiral phosphoric acids were used as the only chiral source to control the stereoselectivity in the C-H activation reactions.

Key words: palladium catalysis, C-H activation, asymmetric catalysis, chiral phosphoric acids, ferrocenes

引用此文

张松, 陆俊筑, 叶金星, 段伟良. 手性磷酸控制的不对称碳氢芳基化反应合成平面手性二茂铁化合物[J]. 有机化学, 2016, 36(4): 752-759.

Zhang Song, Lu Junzhu, Ye Jinxing, Duan Wei-liang. Asymmetric C-H Arylation for the Synthesis of Planar Chiral Ferrocenes: Controlling Enantioselectivity Using Chiral Phosphoric Acids[J]. Chin. J. Org. Chem., 2016, 36(4): 752-759.

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参考文献

[1] For selected reviews on C-H activation, see: (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
(b) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712.
(c) Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191.
(d) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236.
(e) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712.
(f) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654.
(g) Yu, J.-Q.; Shi, Z. C-H Activation, Topics in Current Chemistry, Springer, Berlin, 2010, Vol. 292.
(h) Dastbaravardeh, N.; Christakakou, M.; Haider, M.; Schnürch, M. Synthesis 2014, 46, 1421.
(i) Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283 (in Chinese). (廖港, 史炳锋, 化学学报, 2015, 73, 1283.)
[2] For reviews on enantioselective C-H activation, see: (a) Wencel-Delord, J.; Colobert, F. Chem.-Eur. J. 2013, 19, 14010.
(b) Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927.
(c) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
(d) Pedroni, J.; Cramer, N. Chem. Commun. 2015, 51, 17647.
[3] Giri, R.; Liang, J.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 7420.
[4] For selected examples of Pd-catalyzed enantioselective C-H activation using chiral amino acid as the ligand, see: (a) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
(b) Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460.
(c) Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598.
(d) Musaev, D. G.; Kaledin, A.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 1690.
(e) 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.
(f) Chu, L.; Wang, X.-C.; Moore, C. E.; Rheingold, A. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344.
(g) Chu, L.; Xiao, K.-J.; Yu, J.-Q. Science 2014, 346, 451.
(h) Xiao, K.-J.; Lin, D.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138.
(i) Chan, K. S. L.; Fu, H.-Y.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137, 2042.
[5] (a) Albicker, M. R.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 9139.
(b) Renaudat, A.; Jean-Ge'rard, L.; Jazzar, R.; Kefalidis, C. E.; Clot, E.; Baudoin, O. Angew. Chem., Int. Ed. 2010, 49, 7261.
(c) Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438.
(d) Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483.
(e) Katayev, D.; Nakanishi, M.; Bürgi, T.; Kündig, E. P. Chem. Sci. 2012, 3, 1422.
(f) Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238.
(g) Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem.-Eur. J. 2012, 18, 4480.
(h) Shintani, R.; Otomo, H.; Ota, K.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 7305.
(i) Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 12842.
(j) Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2013, 52, 7865.
(k) Katayev, D.; Jia, Y.-X.; Sharma, A. K.; Banerjee, D.; Besnard, C.; Sunoj, R. B.; Kündig, E. P. Chem.-Eur. J. 2013, 19, 11916.
(l) Larionov, E.; Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Chem. Sci. 2013, 4, 1995.
[6] (a) Hyster, T. K.; Knörr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500.
(b) Ye, B.; Cramer, N. Science 2012, 338, 504.
(c) Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636.
(d) Ye, B.; Donets, P. A.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 507.
(e) Ye, B.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 7896.
[7] For books see: (a) Hayashi, T., Togni, A Ferrocenes, VCH, Weinheim, Germany, 1995.
(b) Št?pni?ka, P. Ferrocenes, Wiley: Chichester, 2008.
(c) Dai, L.-X., Hou, X.-L. Chiral Ferrocenes in Asymmetric Catalysis, Wiley, New York, 2010.
(d) Barlow, S.; O'Hare, D. Chem. Rev. 1997, 97, 637.
(e) Azevedo, C. G.; Vollhardt, K. P. C. Synlett 2002, 1019.
(f) Wang, Y.; Zhang A.; Liu, L.; Kang J.; Zhang, F.; Ma, W. Chin, J. Org. Chem. 2015, 35, 1399 (in Chinese). (王艳芳, 张安安, 刘澜涛, 康建勋, 张富强, 马文瑾, 有机化学, 2015, 35, 1399.)
[8] (a) Siegel, S.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2456.
(b) Günay, M. E.; Richards, C. J. Organometallics 2009, 28, 5833.
(c) Dendele, N.; Bisaro, F.; Gaumont, A.-C.; Perrio, S.; Richards, C. J. Chem. Commun. 2012, 48, 1991.
(d) Takebayashi, S.; Shizuno, T.; Otani, T.; Shibata, T. Beilstein J. Org. Chem. 2012, 8, 1844.
[9] (a) Ogasawara, M.; Watanabe, S.; Fan, L.; Nakajima, K.; Takahashi, T. Organometallics 2006, 25, 5201.
(b) Ogasawara, M.; Watanabe, S.; Nakajima, K.; Takahashi, T. Pure Appl. Chem. 2008, 80, 1109.
(c) Ogasawara, M.; Watanabe, S.; Nakajima, K.; Takahashi, T. J. Am. Chem. Soc. 2010, 132, 2136.
(d) Ogasawara, M.; Wu, W.-Y.; Arae, S.; Watanabe, S.; Morita, T.; Takahashi, T.; Kamikawa, K. Angew. Chem., Int. Ed. 2012, 51, 2951.
(e) Ogasawara, M.; Arae, S.; Watanabe, S.; Nakajima, K.; Takahashi, T. Chem. Eur. J. 2013, 19, 4151.
[10] (a) Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86.
(b) Gao, D.-W.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 2544.
[11] (a) Pi, C.; Li, Y.; Cui, X.-L.; Zhang, H.; Han, Y.-B.; Wu, Y.-J. Chem. Sci. 2013, 4, 2675.
(b) Pi, C.; Cui, X.; Liu, X.; Guo, M.; Zhang, H.; Wu, Y. Org. Lett. 2014, 16, 5164.
[12] (a) Gao, D.-W.; Yin, Q.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2014, 136, 4841.
(b) Deng, R.-X.; Huang, Y.-Z.; Kang, Y.-B.; Gu, Z.-H. J. Am. Chem. Soc. 2014, 136, 4472.
[13] (a) Ma, X.; Gu, Z. RSC Adv. 2014, 4, 36241.
(b) Liu, L.; Zhang, A.-A.; Zhao, R.-J.; Li, F.; Meng, T.-J.; Ishida, N.; Murakami, M.; Zhao, W.-X. Org. Lett. 2014, 16, 5336.
[14] Gao, D.-W.; Zheng, C.; Gu, Q.; You, S.-L. Organometallics 2015, 34, 4618.
[15] Yan, S.-B.; Zhang, S.; Duan, W.-L. Org. Lett. 2015, 17, 2458.
[16] For selected reviews, see: (a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
(b) Terada, M. Chem. Commun. 2008, 4097.
(c) Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S. B. Org. Biomol. Chem. 2010, 8, 5262.
(d) Su, Y.; Shi, F. Chin, J. Org. Chem. 2010, 30, 486 (in Chinese). (苏亚军, 史福, 有机化学, 2010, 30, 486.)
(e) Wu, X.; Li, M.; Gong, L. Acta Chim. Sinica 2013, 71, 1091 (in Chinese). (吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.)
(f) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047 and references therein.
[17] Examples of chiral phosphoric acids as additives in C-H activation reactions: (a) Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.-S.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124.
(b) Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
(c) Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135.
(d) Chen, K.; Shi, B.-F. Angew. Chem., Int. Ed. 2014, 53, 11950.
(e) Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2015, 137, 531. For an example of CPAs-mediated enantioselective cross-dehydro- genative coupling reactions, see:
(f) Neel, A. J.; Hehn, J. P.; Tripet, P. F.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 14044.
[18] For selected reports involving organic phosphate ligands in Pd-catalyzed reactions, see: (a) Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336.
(b) Jiang, G.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9471.
(c) Chai, Z.; Rainey, T. J. J. Am. Chem. Soc. 2012, 134, 3615.
(d) Yu, S.-Y.; Zhang, H.; Gao, Y.; Mo, L.; Wang, S.; Yao, Z.-J. J. Am. Chem. Soc. 2013, 135, 11402.
(e) Zhang, D.; Qiu, H.; Jiang, L.; Lv, F.; Ma, C.; Hu, W. Angew. Chem., Int. Ed. 2013, 52, 13356.
(f) Wang, P. S.; Lin, H.-C.; Zhai, Y.-J.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 12218.
(g) Tao, Z.-L.; Li, X.-H.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 4054.
[19] For reviews or reports on CMD mechanism, see: (a) Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118.
(b) Livendahl, M.; Echavarren, A. M. Isr. J. Chem. 2010, 50, 630.
(c) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
(d) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.
[20] (a) Anas, S.; Cordi, A.; Kagan. H. B. Chem. Commun. 2011, 47, 11483.
(b) Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438.