Reviews

Transition-Metal-Catalyzed Arylation of Unactivated C(sp3)—H Bonds Assisted by Bidentate Directing Groups

  • Zhang Bo ,
  • Guan Hanxi ,
  • Liu Bin ,
  • Shi Bingfeng
Expand
  • Department of Chemistry, Zhejiang university, Hangzhou 310007

Received date: 2014-05-07

  Revised date: 2014-05-30

  Online published: 2014-06-11

Supported by

Project supported by the National Natural Science Foundation of China (No. J1210042) and the Fundamental Research Funds for the Central Universities (No. 2014QNA3008).

Abstract

Recently, transition-metal-catalyzed C—H functionalization has attracted tremendous interest as a valuable tool for carbon-carbon and carbon-heteroatom bond formation. However, due to the inertness of C(sp3)—H bonds and the difficulty to achieving high selectivity among the many chemically similar entities in a given molecule, the selective activation of C(sp3)—H bonds remains a great challenge. The recent progress in transition-metal-catalyzed arylation of unactivated C(sp3)—H bonds assisted by bidentate directing groups is reviewed, including the scope of reactions, mechanism and synthetic applications.

Cite this article

Zhang Bo , Guan Hanxi , Liu Bin , Shi Bingfeng . Transition-Metal-Catalyzed Arylation of Unactivated C(sp3)—H Bonds Assisted by Bidentate Directing Groups[J]. Chinese Journal of Organic Chemistry, 2014 , 34(8) : 1487 -1498 . DOI: 10.6023/cjoc201405011

References

[1] For selected recent reviews, see: (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
(b) Godula, K.; Sames, D. Science 2006, 312, 67.
(c) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Soc. Rev. 2007, 107, 174.
(d) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
(e) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
(f) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(g) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
(h) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(i) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
(j) Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
(k) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(l) Yang, L.; Huang, H. Catal. Sci. Technol. 2012, 2, 1099.
(m) Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936.
(n) Li, D.; He, C.; Cai, H.; Wang, G. 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.)
(o) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
[2] For recent reviews on C(sp3)—H activation, see: (a) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
(b) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654.
(c) Wasa, M.; Engle, K. M.; Yu, J.-Q. Isr. J. Chem. 2010, 50, 605.
(d) Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191.
(e) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902.
(f) Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
[3] (a) Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896.
(b) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
[4] Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
[5] For selected reviews on high-valent Palladium, see: (a) Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412.
(b) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712.
(c) Powers, D. C.; Ritter, T. Acc. Chem. Res. 2012, 45, 840.
[6] Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
[7] Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
[8] Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414.
[9] He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192.
[10] Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed. 2012, 51, 5188.
[11] Rodriguez, N.; Revilla, R. J. A.; FernandezIbanez, M. A.; Carretero, J. C. Chem. Sci. 2013, 4, 175
[12] Xie, Y.-J.; Yang, Y.-Z.; Huang, L.-H.; Zhang, X.-B.; Zhang, Y.-H.; Org. Lett. 2012, 14, 1238.
[13] Fan, M.-Y.; Ma, D.-W. Angew. Chem., Int. Ed. 2013, 52, 12152.
[14] Parella, R.; Gopalakrishnan, B.; Babu, S. A. Org. Lett. 2013, 15, 3238.
[15] Roman, D. S.; Charette, A. B. Org. Lett. 2013, 15, 4394.
[16] Hoshiya, N.; Kobayashi, T.; Arisawa, M.; Shuto, S. Org. Lett. 2013, 15, 6202.
[17] Pan, F.; Shen, P.-X.; Zhang, L.-S.; Wang, X.; Shi, Z.-J. Org. Lett. 2013, 15, 4758.
[18] Zhang, Q.; Chen, K.; Rao, W.-H.; Zhang, Y.-J.; Chen, F.-J.; Shi, B.-F. Angew. Chem., Int. Ed. 2013, 52, 13588.
[19] Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187.
[20] Wei, Y.; Tang, H.; Cong, X.; Rao, B.; Wu, C.; Zeng, X. Org. Lett. 2014, 16, 2248.
[21] Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030.
[22] Gu, Q.; Al Mamari, H. H.; Graczyk, K.; Diers, E.; Ackermann. L. Angew. Chem., Int. Ed. 2014, 53. 3868.
[23] (a)Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 2013, 19.
(b) Nakao, Y.; Morita, E.; Idei, H.; Hiyama, T. J. Am. Chem. Soc. 2011, 133, 3264.
[24] Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898.
[25] Wu, X.-S.; Zhao, Y.; Ge. H.-B. J. Am. Chem. Soc. 2014, 136, 1789.
[26] Li, M.-L.; Dong, J.-X.; Huang, X.-L.; Li, K.-Z.; Wu, Q.; Song, F.-J.; You, J.-S. Chem. Commun. 2014, 50, 3944.
[27] Feng, Y.; Chen, G. Angew. Chem., Int. Ed. 2010, 49, 958.
[28] Li, B. T. Y.; White, J. M.; Hutton, C. A. Aust. J. Chem. 2010, 63, 438.
[29] Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076.
[30] Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507.
[31] Gutekunst, W. R.; Baran, P. S. J. Org. Chem. 2014, 79, 2430.
[32] Parella, R.;Gopalakrishnan, B.; Babu, S. A. J. Org. Chem. 2013, 78, 11911.
[33] Ting, C. P.; Maimone, T. J. Angew. Chem., Int. Ed. 2014, 53, 3115.
[34] 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.)
[35] Chen, K.; Hu, F.; Zhang S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
Outlines

/