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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 2086 - 2093

DOI: https://doi.org/10.6023/cjoc202003058

Efficient Magnesium-Catalyzed Hydroboration of Carboxylic Acids

  • Zheng Yukun ,
  • Cao Xu ,
  • Li Jia ,
  • Hua Haiming ,
  • Yao Weiwei ,
  • Zhao Binlin ,
  • Ma Mengtao
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  • a College of Science, Nanjing Forestry University, Nanjing 210037;
    b College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023

Received date: 2020-03-25

  Revised date: 2020-04-26

  Online published: 2020-05-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21772093, 21372117) and the Natural Science Foundation of Jiangsu Province (No. BK20181421).

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Abstract

Sterically bulky amino magnesium methyl complex, LMgCH3(THF)2 (L=NAr(SiMe3), Ar=4,2,6-Me(CHPh2)2-C6H2) has been employed as an efficient precatalyst for the deoxygenate hydroboration of a variety of aromatic and aliphatic acids with pinacolborane (HBpin) under mild reaction condition. Additionally, chemoselective hydroboration of carboxylic acids over esters was also achieved under the standard conditions. Two plausible reaction mechanisms were proposed based on the density functional theory (DFT) calculations and stoichiometric reactions.

Key words： hydroboration; carboxylic acid; magnesium; main group metal

Cite this article

Zheng Yukun , Cao Xu , Li Jia , Hua Haiming , Yao Weiwei , Zhao Binlin , Ma Mengtao . Efficient Magnesium-Catalyzed Hydroboration of Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2020 , 40(7) : 2086 -2093 . DOI: 10.6023/cjoc202003058

References

[1] Ullrich, J.; Breit, B. ACS Catal. 2018, 8, 785.
[2] Korstanje, T. J.; Vlugt, J. I.; Elsevier, C. J.; de Bruin, B. Science 2015, 350, 298.
[3] Cui, X.; Li, Y.; Topf, C.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 10596.
[4] Stein, T.; Meuresch, M.; Limper, D.; Schmitz, M.; Holscher, M.; Coetzee, J.; Cole-Hamilton, D. J.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2014, 136, 13217.
[5] Brewster, T. P.; Miller, A. J. M.; Heinekey, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2013, 135, 16022.
[6] Zhang, M.; Li, N.; Tao, X.; Ruzi, R.; Yu, S.; Zhu, C. Chem. Commun. 2017, 53, 10228.
[7] Corre, Y.; Rysak, V.; Trivelli, X.; Agbossou-Niedercorn, F.; Michon, C. Eur. J. Org. Chem. 2017, 4820.
[8] Nguyen, T. V. Q.; Yoo, W. J.; Kobayashi, S. Adv. Synth. Catal. 2016, 358, 452.
[9] Fernandez-Salas, J. A.; Manzini, S.; Nolan, S. P. Adv. Synth. Catal. 2014, 356, 308.
[10] Zheng, J.; Chevance, S.; Darcel, C.; Sortais, J. B. Chem. Commun. 2013, 49, 10010.
[11] Misal Castro, L. C.; Li, H.; Sortais, J. B.; Darcel, C. Chem. Commun. 2012, 48, 10514.
[12] Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
[13] Gevorgyan, V.; Rubin, M.; Liu, J. X.; Yamamoto, Y. J. Org. Chem. 2001, 66, 1672.
[14] Chong, C. C.; Kinjo, R. ACS Catal. 2015, 5, 3238.
[15] Bismuto, A.; Cowley, M. J.; Thomas, S. P. ACS Catal. 2018, 8, 2001.
[16] Das, U. K.; Higman, C. S.; Gabidullin, B.; Hein, J. E.; Baker, R. T. ACS Catal. 2018, 8, 1076.
[17] Weidner, V. L.; Barger, C. J.; Delferro, M.; Lohr, T. L.; Marks, T. J. ACS Catal. 2017, 7, 1244.
[18] Barman, M. K.; Baishya, A.; Nembenna, S. Dalton Trans. 2017, 46, 4152.
[19] Lortie, J. L.; Dudding, T.; Gabidullin, B. M.; Nikonov, G. I. ACS Catal. 2017, 7, 8454.
[20] (a) Li, Y.; Cheng, Y.; Shan, C.; Zhang, J.; Xu, D.; Bai, R.; Qu, L.; Lan, Y. Chin. J. Org. Chem. 2018, 38, 1885(in Chinese). (李园园, 程玉华, 单春晖, 张敬, 徐冬冬, 白若鹏, 屈凌波, 蓝宇, 有机化学, 2018, 38, 1885.)
(b) Wang, L.; Sun, W.; Liu, C. Chin. J. Catal. 2018, 39, 1725.
(c) He, Z.; Zhu, Q.; Hu, X.; Wang, L.; Xia, C.; Liu, C. Org. Chem. Front. 2019, 6, 900.
(d) Xuan, Q.; Song, Q. Org. Lett. 2016, 18, 4250.
(e) Luo, M.; Zang, S.; Yao, W.; Zheng, J.; Ma, M. Sci. Sin. Chim. 2020, 50, 639.
[21] Kishan, S.; KrishnaKumar, V.; Gunanathan, C. ACS Catal. 2018, 8, 4772.
[22] (a) Erken, C.; Kaithal, A.; Sen, S.; Weyhermüller, T.; Hölscher, M.; Werlé, C.; Leitner, W. Nat. Commun. 2018, 9, 4521.
(b) Barman, M. K.; Das, K.; Maji, B. J. Org. Chem. 2019, 84, 1570.
[23] (a) Harinath, A.; Bhattacharjee, J.; Panda, T. K. Chem. Commun. 2019, 55, 1386.
(b) Wang, W.; Luo, M.; Zhu, D.; Yao, W.; Xu, L.; Ma, M. Org. Biomol. Chem. 2019, 17, 3604.
(c) Xu, X.; Yan, D.; Zhu, Z.; Kang, Z.; Yao, Y.; Shen, Q.; Xue, M. ACS Omega. 2019, 4, 6775.
[24] Power, P. P. Nature 2010, 463, 171.
[25] Ma, M.; Li, J.; Shen, X.; Yu, Z.; Yao, W.; Pullarkat, S. A. RSC Adv. 2017, 7, 45401.
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