Citation: Xu Yuliang, Fang Hao. Research Progress towards Synthesis of Aryl Boronic Acid Compounds[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 738-751. doi: 10.6023/cjoc201709045 shu

Research Progress towards Synthesis of Aryl Boronic Acid Compounds

Xu Yuliang ,
Fang Hao ^,

a.
Key Laboratory of Chemical Biology (Ministry of Education), Shandong University, Jinan 250012
b.
Department of Medicinal Chemistry, School of Pharmacy, Shandong University, Jinan 250012

Corresponding author: Fang Hao, haofangcn@sdu.edu.cn
Received Date: 28 September 2017
Revised Date: 11 November 2017
Available Online: 5 April 2017
Fund Project: Project supported by the National Natural Science Foundation of China 21672127Project supported by the National Natural Science Foundation of China (No. 21672127)

Figures(15)

Aromatic boronic acids and esters are essential intermediates and have been widely used in biology, medicine and material science. In this paper, the resent progress on their synthesis is summarized, especially Pd-catalyzed borylation of aryl chlorides with steric hindrance substrates, other metal (Ni, Cu, Fe, Zn, Rh, Co)-catalyzed borylation, metal-free borylation, and photoinduced borylation.
- aromatic boronic acids,
- metal-catalyzed,
- metal-free catalyzed,
- photoinduced
1. [1]
  (a) Lacina, K. ; Skladal, P. ; James, T. D. Chem. Cent. J. 2014, 8, 60.
  (b) Li, D. -J. ; Chen, Y. ; Liu, Z. Chem. Soc. Rev. 2015, 44, 8097.
  (c) Sun, X. ; Zhai, W. ; Fossey, J. S. ; James, T. D. Chem. Commun. 2016, 52, 3456.
2. [2]
  Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007
3. [3]
  Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. doi: 10.1021/jo00128a024
4. [4]
  Murata, M. Heterocycles 2012, 85, 1795. doi: 10.3987/REV-12-736
5. [5]
  Chow, W. K.; Yuen, O. Y.; Choy, P. Y.; So, C. M.; Lau, C. P.; Wong, W. T.; Kwong, F. Y. RSC Adv. 2013, 3, 12518. doi: 10.1039/c3ra22905j
6. [6]
  Kubota, K.; Iwamoto, H.; Ito, H. Org. Biomol. Chem. 2017, 15, 285. doi: 10.1039/C6OB02369J
7. [7]
  Li, P.; Meng, G.; Chen, K.; Wang, L. Synthesis 2017, 49, 4719. doi: 10.1055/s-0036-1590913
8. [8]
  Yan, G.-B.; Huang, D.-Y.; Wu, X.-M. Adv. Synth. Catal. 2018, 360, 1040. doi: 10.1002/adsc.v360.6
9. [9]
  (a) Ros, A. ; Fernandez, R. ; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229.
  (b) Xu, L. ; Wang, G. -H. ; Zhang, S. ; Wang, H. ; Wang, L. -H. ; Liu, L. ; Jiao, J. ; Li, P. -F. Tetrahedron 2017, 73, 7123.
10. [10]
  (a) Ishiyama, T. ; Itoh, Y. ; Kitano, T. ; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447.
  (b) Murata, M. ; Watanabe, S. ; Masuda, Y. J. Org. Chem. 1997, 62, 6458.
  (c) Willis, D. M. ; Strongin, R. M. Tetrahedron Lett. 2000, 41, 8683.
11. [11]
  Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813. doi: 10.1016/S0040-4020(01)00998-X
12. [12]
  Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359. doi: 10.1002/(ISSN)1521-3773
13. [13]
  Billingsley, K. L.; Buchwald, S. L. J. Org. Chem. 2008, 73, 5589.
14. [14]
  (a) Molander, G. A. ; Trice, S. L. ; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701.
  (b) Molander, G. A. ; Trice, S. L. J. ; Kennedy, S. M. ; Dreher, S. D. ; Tudge, M. T. J. Am. Chem. Soc. 2012, 134, 11667.
15. [15]
  Chow, W. K.; Yuen, O. Y.; So, C. M.; Wong, W. T.; Kwong, F. Y. J. Org. Chem. 2012, 77, 3543. doi: 10.1021/jo202472k
16. [16]
  Yamamoto, Y.; Matsubara, H.; Yorimitsu, H.; Osuka, A. ChemCat-Chem 2016, 8, 2317. doi: 10.1002/cctc.201600456
17. [17]
  Baudoin, O.; Guénard, D.; Guéritte, F. J. Org. Chem. 2000, 65, 9268. doi: 10.1021/jo005663d
18. [18]
  Fang, H.; Kaur, G.; Yan, J.; Wang, B. Tetrahedron Lett. 2005, 46, 1671. doi: 10.1016/j.tetlet.2005.01.064
19. [19]
  Rodriguez, S.; Qu, B.; Haddad, N.; Reeves, D. C.; Tang, W.-J.; Lee, H.; Krishnamurthy, D.; Senanayake, C. H. Adv. Synth. Catal. 2011, 353, 533. doi: 10.1002/adsc.201000878
20. [20]
  Kawamorita, S.; Ohmiya, H.; Iwai, T.; Sawamura, M. Angew. Chem., Int. Ed. 2011, 50, 8363. doi: 10.1002/anie.v50.36
21. [21]
  Morgan, A. B.; Jurs, J. L.; Tour, J. M. J. Appl. Polym. Sci. 2000, 76, 1257. doi: 10.1002/(ISSN)1097-4628
22. [22]
  Rosen, B. M.; Huang, C.; Percec, V. Org. Lett. 2008, 10, 2597. doi: 10.1021/ol800832n
23. [23]
  Moldoveanu, C.; Wilson, D. A.; Wilson, C. J.; Corcoran, P.; Rosen, B. M.; Percec, V. Org. Lett. 2009, 11, 4974. doi: 10.1021/ol902155e
24. [24]
  Yamamoto, T.; Morita, T.; Takagi, J.; Yamakawa, T. Org. Lett. 2011, 13, 5766. doi: 10.1021/ol202267t
25. [25]
  Molander, G. A.; Cavalcanti, L. N.; Garcia-Garcia, C. J. Org. Chem. 2013, 78, 6427. doi: 10.1021/jo401104y
26. [26]
  Zhang, H.; Hagihara, S.; Itami, K. Chem.-Eur. J. 2015, 21, 16796. doi: 10.1002/chem.v21.47
27. [27]
  Hu, J.-F.; Sun, H.-Q.; Cai, W.-S.; Pu, X.-H.; Zhang, Y.-M.; Shi, Z.-Z. J. Org. Chem. 2016, 81, 14. doi: 10.1021/acs.joc.5b02557
28. [28]
  Liu, X.-W.; Echavarren, J.; Zarate, C.; Martin, R. J. Am. Chem. Soc. 2015, 137, 12470. doi: 10.1021/jacs.5b08103
29. [29]
  Tobisu, M.; Zhao, J.-N.; Kinuta, H.; Furukawa, T.; Igarashi, T.; Chatani, N. Adv. Synth. Catal. 2016, 358, 2417. doi: 10.1002/adsc.201600336
30. [30]
  Hu, J.; Zhao, Y.; Liu, J.; Zhang, Y.; Shi, Z. Angew. Chem., Int. Ed. Engl. 2016, 55, 8718. doi: 10.1002/anie.201603068
31. [31]
  Pu, X.-H.; Hu, J.-F.; Zhao, Y.; Shi, Z.-Z. ACS Catal. 2016, 6, 6692. doi: 10.1021/acscatal.6b01956
32. [32]
  Guo, L.; Rueping, M. Chem.-Eur. J. 2016, 22, 16787. doi: 10.1002/chem.v22.47
33. [33]
  Zhu, W.; Ma, D.-W. Org. Lett. 2006, 8, 261. doi: 10.1021/ol052633u
34. [34]
  Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350. doi: 10.1002/anie.200901879
35. [35]
  Yan, G.-B.; Yang, M.-H.; Yu, J. Lett. Org. Chem. 2012, 9, 71. doi: 10.2174/157017812799304015
36. [36]
  Yu, H.; Zhang, J.; Wang, X.; Ye, J. Synlett 2012, 23, 1394. doi: 10.1055/s-0031-1290960
37. [37]
  Nagashima, Y.; Takita, R.; Yoshida, K.; Hirano, K.; Uchiyama, M. J. Am. Chem. Soc. 2013, 135, 18730. doi: 10.1021/ja409748m
38. [38]
  Bose, S. K.; Marder, T. B. Org. Lett. 2014, 16, 4562. doi: 10.1021/ol502120q
39. [39]
  Bose, S. K.; Deissenberger, A.; Eichhorn, A.; Steel, P. G.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2015, 54, 11843. doi: 10.1002/anie.201505603
40. [40]
  Qi, X.-X.; Jiang, L.-B.; Zhou, C.; Peng, J.-B.; Wu, X.-F. ChemistryOpen 2017, 6, 345. doi: 10.1002/open.v6.3
41. [41]
  Tobisu, M.; Kinuta, H.; Kita, Y.; Remond, E.; Chatani, N. J. Am. Chem. Soc. 2012, 134, 115. doi: 10.1021/ja2095975
42. [42]
  Kinuta, H.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2015, 137, 1593. doi: 10.1021/ja511622e
43. [43]
  Marciasini, L. D.; Richy, N.; Vaultier, M.; Pucheault, M. Adv. Synth. Catal. 2013, 355, 1083. doi: 10.1002/adsc.v355.6
44. [44]
  Bedford, R. B.; Brenner, P. B.; Carter, E.; Gallagher, T.; Murphy, D. M.; Pye, D. R. Organometallics 2014, 33, 5940. doi: 10.1021/om500847j
45. [45]
  Yoshida, T.; Ilies, L.; Nakamura, E. ACS Catal. 2017, 7, 3199. doi: 10.1021/acscatal.7b00310
46. [46]
  Yao, W.-B.; Fang, H.-Q.; Peng, S.-H.; Wen, H.-N.; Zhang, L.; Hu, A.-G.; Huang, Z. Organometallics 2016, 35, 1559. doi: 10.1021/acs.organomet.6b00161
47. [47]
  Komeyama, K.; Kiguchi, S.; Takaki, K. Chem. Commun. 2016, 52, 7009. doi: 10.1039/C6CC03086F
48. [48]
  Mo, F.-Y.; Jiang, Y.-B.; Qiu, D.; Zhang, Y.; Wang, J.-B. Angew. Chem., Int. Ed. 2010, 49, 1846. doi: 10.1002/anie.v49:10
49. [49]
  Qiu, D.; Jin, L.; Zheng, Z.-T.; Meng, H.; Mo, F.-Y.; Wang, X.; Zhang, Y.; Wang, J.-B. J. Org. Chem. 2013, 78, 1923. doi: 10.1021/jo3018878
50. [50]
  Zhu, C.; Yamane, M. Org. Lett. 2012, 14, 4560. doi: 10.1021/ol302024m
51. [51]
  Erb, W.; Hellal, A.; Albini, M.; Rouden, J.; Blanchet, J. Chem.-Eur. J. 2014, 20, 6608. doi: 10.1002/chem.v20.22
52. [52]
  Zhao, C.-J.; Xue, D.; Jia, Z.-H.; Wang, C.; Xiao, J. Synlett 2014, 25, 1577. doi: 10.1055/s-00000083
53. [53]
  Yamamoto, E.; Izumi, K.; Horita, Y.; Ito, H. J. Am. Chem. Soc. 2012, 134, 19997. doi: 10.1021/ja309578k
54. [54]
  Yamamoto, E.; Ukigai, S.; Ito, H. Chem. Sci. 2015, 6, 2943. doi: 10.1039/C5SC00384A
55. [55]
  Uematsu, R.; Yamamoto, E.; Maeda, S.; Ito, H.; Taketsugu, T. J. Am. Chem. Soc. 2015, 137, 4090. doi: 10.1021/ja507675f
56. [56]
  Zhang, J.-M.; Wu, H.-H.; Zhang, J.-L. Eur. J. Org. Chem. 2013, 6263.
57. [57]
  Lee, Y.; Baek, S. Y.; Park, J.; Kim, S. T.; Tussupbayev, S.; Kim, J.; Baik, M. H.; Cho, S. H. J. Am. Chem. Soc. 2017, 139, 976. doi: 10.1021/jacs.6b11757
58. [58]
  Zhang, L.; Jiao, L. J. Am. Chem. Soc. 2017, 139, 607. doi: 10.1021/jacs.6b11813
59. [59]
  Pucheault, M.; Pinet, S.; Liautard, V.; Debiais, M. Synthesis 2017, 49, 4759. doi: 10.1055/s-0036-1588431
60. [60]
  Miralles, N.; Romero, R. M.; Fernández, E.; Mu iz, K. Chem. Commun. 2015, 51, 14068. doi: 10.1039/C5CC04944J
61. [61]
  Cheng, W.-M.; Shang, R.; Zhao, B.; Xing, W.-L.; Fu, Y. Org. Lett. 2017, 19, 4291. doi: 10.1021/acs.orglett.7b01950
62. [62]
  Chen, K.; Zhang, S.; He, P.; Li, P.-F. Chem. Sci. 2016, 7, 3676. doi: 10.1039/C5SC04521E
63. [63]
  Chen, K.; Cheung, M. S.; Lin, Z.-Y.; Li, P.-F. Org. Chem. Front. 2016, 3, 875. doi: 10.1039/C6QO00109B
64. [64]
  Mfuh, A. M.; Doyle, J. D.; Chhetri, B.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2016, 138, 2985. doi: 10.1021/jacs.6b01376
65. [65]
  Liu, W.-B.; Yang, X.-B.; Gao, Y.; Li, C.-J. J. Am. Chem. Soc. 2017, 139, 8621. doi: 10.1021/jacs.7b03538
66. [66]
  Yu, J.; Zhang, L.; Yan, G.-B. Adv. Synth. Catal. 2012, 354, 2625. doi: 10.1002/adsc.v354.14/15
67. [67]
  Ahammed, S.; Nandi, S.; Kundu, D.; Ranu, B. C. Tetrahedron Lett. 2016, 57, 1551. doi: 10.1016/j.tetlet.2016.02.097
68. [68]
  Jiang, M.; Yang, H.-J.; Fu, H. Org. Lett. 2016, 18, 5248. doi: 10.1021/acs.orglett.6b02553
69. [69]
  Teders, M.; Pitzer, L.; Hopkinson, M. N.; Glorius, F. Angew. Chem., Int. Ed. 2017, 56, 902. doi: 10.1002/anie.201609393
70. [70]
  Hu, D.-W.; Wang, L.-H.; Li, P.-F. Org. Lett. 2017, 19, 2770. doi: 10.1021/acs.orglett.7b01181
71. [71]
  Candish, L.; Teders, M.; Glorius, F. J. Am. Chem. Soc. 2017, 139, 7440. doi: 10.1021/jacs.7b03127
72. [72]
  Fawcett, A.; Pradeilles, J.; Wang, Y.; Mutsuga, T.; Myers, E. L.; Aggarwal, V. K. Science 2017, 357, 283. doi: 10.1126/science.aan3679
1. [1]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
2. [2]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
3. [3]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
4. [4]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
5. [5]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
6. [6]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
7. [7]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
8. [8]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
9. [9]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
10. [10]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
11. [11]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
12. [12]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
13. [13]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
14. [14]
  Tianlong Zhang , Jiajun Zhou , Hongsheng Tang , Xiaohui Ning , Yan Li , Hua Li . Virtual Simulation Experiment for Laser-Induced Breakdown Spectroscopy (LIBS) Analysis. University Chemistry, 2024, 39(6): 295-302. doi: 10.3866/PKU.DXHX202312049
15. [15]
  Xinyu Miao , Hao Yang , Jie He , Jing Wang , Zhiliang Jin . Adjusting the electronic structure of Keggin-type polyoxometalates to construct S-scheme heterojunction for photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(6): 100051-. doi: 10.1016/j.actphy.2025.100051
16. [16]
  Lubing Qin , Fang Sun , Meiyin Li , Hao Fan , Likai Wang , Qing Tang , Chundong Wang , Zhenghua Tang . 原子精确的(AgPd)₂₇团簇用于硝酸盐电还原制氨：一种配体诱导策略来调控金属核. Acta Physico-Chimica Sinica, 2025, 41(1): 2403008-. doi: 10.3866/PKU.WHXB202403008
17. [17]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
18. [18]
  Caiyun Jin , Zexuan Wu , Guopeng Li , Zhan Luo , Nian-Wu Li . 用于金属锂电池的磷腈基阻燃人工界面层. Acta Physico-Chimica Sinica, 2025, 41(8): 100094-. doi: 10.1016/j.actphy.2025.100094
19. [19]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
20. [20]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
亮点评述.docx

Get Citation

PDF

XML

Metrics

PDF Downloads(226)
Abstract views(8888)
HTML views(4609)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142