Chinese Journal of Organic Chemistry >
Recent Development of Metal-Free Direct Asymmetric Functionalization of Benzylic C(sp3)—H Bond
Received date: 2016-10-08
Revised date: 2016-12-18
Online published: 2016-12-21
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21402027, 21502019), the Natural Science Foundation of Fujian Province (No. 2015J05046), the Chemicals and Science Foundation for Distinguished Young Scholars of Fujian Agriculture and Forestry University (No. xjq201503).
Compounds containing aryl structures are important organic synthesis intermediates, which are widely present in a large family of natural products and bioactive molecules. In recent years, direct asymmetric functionalization of benzylic C(sp3)—H bond for the efficient construction of arene and hetero-arene motifs with high stereoselectivity has drawn widespread concern from chemical community. Among the various strategies, small molecule-catalyzed metal-free functionalization of benzylic C(sp3)—H bond represents a more challenging but promising transformations. This review is intended to summarize and discuss the most recent advances in this area.
Jiang Xin , Wang Sidun , Guo Guimin , Lu Beili . Recent Development of Metal-Free Direct Asymmetric Functionalization of Benzylic C(sp3)—H Bond[J]. Chinese Journal of Organic Chemistry, 2017 , 37(4) : 841 -857 . DOI: 10.6023/cjoc201610010
[1] (a) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. Eur. J. 2010, 16, 2654.
(b) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.
(c) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(d) Davies, H. M. L.; Morton, D. J. Org. Chem. 2016, 81, 343.
(e) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
(f) Wang, M.; Wang, Z.; Shang, M.; Dai, H. Chin. J. Org. Chem. 2015, 35, 570 (in Chinese).
(王明明, 王子潇, 商明, 戴辉雄, 有机化学, 2015, 35, 570.)
(g) Tan, M.; Gu, Y.; Luo, X.; Zhang, P. Chin. J. Org. Chem. 2015, 35, 781 (in Chinese).
(谭明雄, 顾运琼, 罗旭健, 张培, 有机化学, 2015, 35, 781.)
(h) Chen, T.; Zhang, M. Chin. J. Org. Chem. 2015, 35, 813 (in Chinese).
(陈天保, 章明, 有机化学, 2015, 35, 813.)
(i) Zhao, J.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235 (in Chinese).
(赵金钵, 张前, 化学学报, 2015, 73, 1235.)
(j) Shang, X.; Liu, Z. Acta Chim. Sinica 2015, 73, 1275 (in Chinese).
(尚筱洁, 柳忠全, 化学学报, 2015, 73, 1275.)
[2] (a) Davies, H. M. L.; Lian, Y. Acc. Chem. Res. 2012, 45, 923.
(b) Motevalli, S.; Sokeirik, Y.; Ghanem, A. Eur. J. Org. Chem. 2016, 1459.
(c) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308.
(d) He, G.; Wang, B.; Nack, W. A.; Chen, G. Acc. Chem. Res. 2016, 49, 635.
[3] (a) Retamosa, M. G.; Matador, E.; Monge, D.; Lassaletta, J. M.; Fernandez, R. Chem. Eur. J. 2016, 22, 13430.
(b) Bulfield, D.; Huber, S. M. Chem. Eur. J. 2016, 22, 14434.
(c) Tanriver, G.; Dedeoglu, B.; Catak, S.; Aviyente, V. Acc. Chem. Res. 2016, 49, 1250.
(d) Donslund, B. S.; Johansen, T. K.; Poulsen, P. H.; Halskov, K. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2015, 54, 13860.
[4] (a) Zhao, Y.-L.; Wang, Y.; Luo, Y.-C.; Fu, X.-Z.; Xu, P.-F. Tetrahedron Lett. 2015, 56, 3703.
(b) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173 (c) Wei, G.; Basheer, C.; Tan, C.-H.; Jiang, Z. Tetrahedron Lett. 2016, 57, 3801.
[5] (a) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
(b) Stockerla, S.; Mancheño, O. G. Org. Chem. Front. 2016, 3, 277.
(c) Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Chem. Soc. 2003, 125, 15312.
[6] Benfatti, F.; Capdevila, M. G.; Zoli, L.; Benedetto, E.; Cozzi, P. G. Chem. Commun. 2009, 5919.
[7] Ho, X.-H.; Mho, S.; Kang, H.; Jang, H.-Y. Eur. J. Org. Chem. 2010, 4436.
[8] Zhang, B.; Xiang, S.-K.; Zhang, L.-H.; Cui, Y.; Jiao, N. Org. Lett. 2011, 13, 5212.
[9] Huang, F.; Xu, L.; Xiao, J. Chin. J. Chem. 2012, 30, 2721.
[10] Pan, Y.; Kee, C. W.; Chen, L.; Tan, C.-H. Green Chem. 2011, 13, 2682.
[11] Neel, A. J.; Hehn, J. P.; Tripet, P. F.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 14044.
[12] Zhang, G.; Ma, Y.; Wang, S.; Kong, W.; Wang, R. Chem. Sci. 2013, 4, 2645.
[13] Meng, Z.; Sun, S.; Yuan, H.; Lou, H.; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 543.
[14] Liu, X.; Meng, Z.; Li, C.; Lou, H.; Liu, L. Angew. Chem., Int. Ed. 2015, 54, 6012.
[15] Liu, X.; Sun, S.; Meng, Z.; Lou, H.; Liu, L. Org. Lett. 2015, 17, 2396.
[16] Xie, Z.; Zan, X.; Sun, S.; Pan, X.; Liu, L. Org. Lett. 2016, 18, 3944.
[17] (a) Xiao, J. ChemCatChem 2012, 4, 612.
(b) Nielsen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, S.; Jørgensen, K. A. Chem. Commun. 2011, 47, 632.
[18] Hayashi, Y.; Itoh, T.; Ishikawa, H. Angew. Chem., Int. Ed. 2011, 50, 3920.
[19] Zhang, S.-L.; Xie, H.-X.; Zhu, J.; Li, H.; Zhang, X.-S.; Li, J.; Wang, W. Nat. Commun. 2011, 2, 211.
[20] Zeng, X.; Ni, Q.; Raabe, G.; Enders, D. Angew. Chem., Int. Ed. 2013, 52, 2977.
[21] Mo, J.; Shen, L.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8588.
[22] Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W. Y.; Chi, Y. R. Nat. Chem. 2013, 5, 835.
[23] Fu, Z.; Jiang, K.; Zhu, T.; Torres, J.; Chi, Y. R. Angew. Chem., Int. Ed. 2014, 53, 6506.
[24] Jin, Z.; Chen, S.; Wang, Y.; Zheng, P.; Yang, S.; Chi, Y. R. Angew. Chem., Int. Ed. 2014, 53, 13506.
[25] Xie, Y.; Yu, C.; Li, T.; Tu, S.; Yao, C. Chem. Eur. J. 2015, 21, 5355.
[26] Wang, M. ChemCatChem 2013, 5, 1291.
[27] Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847.
[28] Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 6166.
[29] Kang, Y. K.; Kim, D. Y. Chem. Commun. 2014, 50, 222.
[30] Jaworski, A. A.; Scheidt, K. A. J. Org. Chem. 2016, 81, 10145.
[31] Williams, R. M.; Rollins, S. B.; Judd, T. C. Tetrahedron 2000, 56, 521.
[32] Liu, Y.; Nappi, M.; Arceo, E.; Vera, S.; Melchiorre, P. J. Am. Chem. Soc. 2011, 133, 15212.
[33] Liu, Y.; Nappi, M.; Escudero-Adán, E. C.; Melchiorre, P. Org. Lett. 2012, 14, 1310.
[34] Xiao, Y.-C.; Zhou, Q.-Q.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2012, 14, 5940.
[35] Li, T.; Zhu, J.; Wu, D.; Li, X.; Wang, S.; Li, H.; Li, J.; Wang, W. Chem. Eur. J. 2013, 19, 9147.
[36] Dell'Amico, L.; Companyó, X.; Naicker, T.; Bräuer, T. M.; Jørgensen, K. A. Eur. J. Org. Chem. 2013, 5262.
[37] Raja, A.; Hong, B.-C.; Lee, G.-H. Org. Lett. 2014, 16, 5756.
[38] Skrzyńska, A.; Przydacz, A.; Albrecht, ?. Org. Lett. 2015, 17, 5682.
[39] Chen, X.; Yang, S.; Song, B.-A.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 11134.
[40] Xu, J.; Yuan, S.; Miao, M. Org. Lett. 2016, 18, 3822.
/
〈 |
|
〉 |