Reviews

Recent Progress on Cu-Catalyzed Asymmetric Conjugate Borylation to α,β-Unsaturated Compounds

  • Liu Qiang ,
  • Tian Bing ,
  • Tian Ping ,
  • Tong Xiaofeng ,
  • Lin Guo-Qiang
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  • a Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai 200237;
    b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2014-09-09

  Revised date: 2014-09-30

  Online published: 2014-10-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21372243, 21102161).

Abstract

Organoborons are an important class of organic compounds, because organoboronic acids and their derivatives can be readily converted into a wide variety of functionalities in a stereospecific manner. Cu-catalyzed asymmetric conjugate borylation of unsaturated compounds with bis(pinacolato)diboron (B2pin2) has emerged as a novel synthetic tool to afford a variety of organoboron compounds. Herein, this research progress, which involves using bisphosphine, N-heterocyclic carbine, and other chiral ligands, is summarized.

Cite this article

Liu Qiang , Tian Bing , Tian Ping , Tong Xiaofeng , Lin Guo-Qiang . Recent Progress on Cu-Catalyzed Asymmetric Conjugate Borylation to α,β-Unsaturated Compounds[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 1 -14 . DOI: 10.6023/cjoc201409019

References

[1] (a) Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 45, 6704. (b) Yang, J.; Deng, M.; Yu, T. Chin. J. Org. Chem. 2013, 33, 693 (in Chinese). (杨军, 邓敏智, 于涛, 有机化学, 2013, 33, 693.)
[2] Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024.
[3] (a) Lawson, Y. G.; Lesley, M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R. Chem. Commun. 1997, 2051. (b) Ali, H. A.; Goldberg, I.; Srebnik, M. Organometallics 2001, 20, 3962.
[4] Kabalka, G. W.; Das, B. C.; Das, S. Tetrahedron Lett. 2002, 43, 2323.
[5] (a) Takahashi, K.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 982. (b) Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47. (c) Mun, S.; Lee, J.-E.; Yun, J. Org. Lett. 2006, 8, 4887. (d) Lee, J.-E.; Kwon, J.; Yun, J. Chem. Commun. 2008, 733. (e) Chea, H.; Sim, H.-S.; Yun, J. Adv. Synth.Catal. 2009, 351, 855. (f) Gao, M.; Thorpe, S. B.; Santos, W. L. Org. Lett. 2009, 11, 3478.
[6] Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 5031.
[7] Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W. Organolithium Methods, Academic Press, London, 1988.
[8] Nöth, H. In Product Subclass 4: Metalloboranes, Ed.: Kaufmann, D. E., Thieme, Stuttgart, 2005, pp. 139~178.
[9] (a) Auten, R. W.; Kraus, C. A. J. Am. Chem. Soc. 1952, 74, 3398. (b) Williams, J. L. R.; Doty, J. C.; Grisdale, P.; Searle, J. R.; Regan, T. H.; Happ, G. P.; Maier, D. P. J. Am. Chem. Soc. 1967, 89, 5153. (c) Weber, L.; Schnieder, M.; Lönnecke, P. J. Chem. Soc., DaltonTrans. 2001, 3459.
[10] (a) Köster, R.; Benedikt, G. Angew. Chem., Int. Ed. 1963, 2, 219. (b) Köster, R.; Benedikt, G. Angew. Chem., Int. Ed. 1964, 3, 515. (c) Parsons, T. D.; Self, J. M.; Schaad, L. H. J. Am. Chem. Soc. 1967, 89, 3446. (d) Gragg, B. R.; Ryschkewitsch, G. E. Inorg. Chem. 1976, 15, 1209. (e) Blumenthal, A.; Bissinger, P.; Schmidbaur, H. J. Organomet. Chem. 1993, 462, 107. (f) Imamoto, T.; Hikosaka, T. J. Org. Chem. 1994, 59, 6753. (g) Unverzagt, M.; Subramanian, G.; Hofmann, M.; von Rague Schleyer, P.; Berger, S.; Harms, K.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. 1997, 36, 1469.
[11] Segawa, Y.; Yamashita, M.; Nozaki, K. Science 2006, 314, 113.
[12] Ito, H.; Yamanaka, H.; Tateiwa , J.-i.; Hosomi, A. Tetrahedron Lett. 2000, 41, 6821.
[13] Takahashi, K.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 29, 982.
[14] Laitar, D. S.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196.
[15] Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2008, 47, 145.
[16] Sim, H.-S.; Feng, X.; Yun, J. Chem. Eur. J. 2009, 15, 1939.
[17] Zhao, H.; Dang, L.; Marder, T. B.; Lin, Z. J. Am. Chem. Soc. 2008, 130, 5586.
[18] Fleming, W. J.; Müller-Bunz, H. M.; Lillo, V.; Fernández, E.; Guiry, P. J. Org. Biomol. Chem. 2009, 7, 2520.
[19] Chen, I.-H.; Yin, L.; Itano, W.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 11664.
[20] Feng, X.; Yun, J. Chem. Commun. 2009, 45, 6577.
[21] Feng, X.; Yun, J. Chem. Eur. J. 2010, 16, 13609.
[22] Moure, A. L.; Arrayás, R. G.; Carretero, J. C. Chem. Commun. 2011, 47, 6701.
[23] Burns, A. R.; González, J. S.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 10827.
[24] He, Z.-T.; Zhao, Y.-S.; Tian, P.; Wang, C.-C.; Dong, H.-Q.; Lin, G.-Q. Org. Lett. 2014, 16, 1426.
[25] Luo, Y.; Roy, I. D.; Madec, A. G. E.; Lam, H. W. Angew. Chem., Int. Ed. 2014, 53, 4186.
[26] Lillo, V.; Prieto, A.; Bonet, A.; Díaz-Requejo, M. M.; Ramírez, J.; Pérez , P. J.; Fernández, E. Organometallics 2009, 28, 659.
[27] O'Brien, J. M.; Lee, K.-s; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10630.
[28] Park, J. K.; Lackey, H. H.; Rexford, M. D.; Kovnir, K.; Shatruk, M.; McQuade, D. T. Org. Lett. 2010, 12, 5008.
[29] Hong, B.; Ma, Y.; Zhao, L.; Duan, W.; He, F.; Song, C. Tetrahedron: Asymmetry 2011, 22, 1055.
[30] Zhao, L.; Ma, Y.; Duan, W.; He, F.; Chen, J.; Song, C. Org. Lett. 2012, 14, 5780.
[31] Zhao, L.; Ma, Y.; He, F.; Duan, W.; Chen, J.; Song, C. J. Org. Chem. 2013, 78, 1677.
[32] Zhang, J.-L.; Chen, L.-A; Xu, R.-B.; Wang, C.-F.; Ruan, Y.-P.; Wang, A.-E.; Huang, P.-Q. Tetrahedron: Asymmetry 2013, 24, 492.
[33] Iwai, T.; Akiyama, Y.; Sawamura, M. Tetrahedron: Asymmetry 2013, 24, 729.
[34] Chen, I.-H.; Kanai, M.; Shibasaki, M. Org. Lett. 2010, 12, 4098.
[35] Kobayashi, S.; Xu, P.; Endo, T.; Ueno, M.; Kitanosono, T. Angew. Chem., Int. Ed. 2012, 51, 12763.
[36] Sole, C.; Bonet, A.; de Vries, A. H. M.; de Vries, J. G.; Lefort, L.; Gulyás, H.; Fernández, E. Organometallics 2012, 31, 7855.
[37] Kitanosono, T.; Xu, P.; Kobayashi, S. Chem. Commun. 2013, 49, 8184.

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