Citation: Shi Dunfa, Wang Lu, Xia Chungu, Liu Chao. Recent Advances in Visible-Light-Promoted Transformation of Alkyl Boron Compounds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3605-3619. doi: 10.6023/cjoc202006033 shu

Recent Advances in Visible-Light-Promoted Transformation of Alkyl Boron Compounds

Shi Dunfa ^a,b ,
Wang Lu ^a ,
Xia Chungu ^a ,
Liu Chao ^a,,

a.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
b.
University of Chinese Academy of Sciences, Beijing 100049

Corresponding author: Liu Chao, chaoliu@licp.cas.cn
Received Date: 18 June 2020
Revised Date: 29 August 2020
Available Online: 8 September 2020
Fund Project: National Natural Science Foundation of China 21673261National Natural Science Foundation of China 91745110National Natural Science Foundation of China 21872156Natural Science Foundation of Jiangsu Province BK20181194Youth Innovation Promotion Association of the Chinese Academy of Sciences 2018458Project supported by the National Natural Science Foundation of China (Nos. 21673261, 91745110, 21872156), the Natural Science Foundation of Jiangsu Province (Nos. BK20190002, BK20181194) and the Youth Innovation Promotion Association of the Chinese Academy of Sciences (No. 2018458)Natural Science Foundation of Jiangsu Province BK20190002

Figures(31)

Organoboron compounds are valuable synthetic intermediates and widely used in the synthesis of medicine, pesticide and organic optoelectronic materials due to their extensive resouce and highly transformable ability. Among various organoboron compounds, the synthesis and transformation of alkylboron compounds have attracted much attention. As a sustainable and green energy, visible light shows an important effect in organic systhesis. Tetracoordinated alkylboron compounds could occur single electron transfer (SET) process to generate alkyl radical for further transformations. Herein, the recent advances in the photoinduced transformation of alkyl boron compounds are summarized.
- boron,
- photocatalysis,
- radical,
- single electron transfer
1. [1]
  Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437. doi: 10.1016/S0040-4039(01)95429-2
2. [2]
  Brown, H. C.; Tierney, P. A. J. Am. Chem. Soc. 1958, 80, 1552. doi: 10.1021/ja01540a011
3. [3]
  (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
  (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
  (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
4. [4]
  Zweifel, G.; Arzoumanian, H.; Whitney, C. C. J. Am. Chem. Soc. 1967, 89, 3652. doi: 10.1021/ja00990a061
5. [5]
  Lennox, A. J.; Lloyd-Jones, G. C. Chem. Soc. Rev. 2014, 43, 412. doi: 10.1039/C3CS60197H
6. [6]
  (a) Leonori, D.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2015, 54, 1082.
  (b) Sandford, C.; Aggarwal, V. K. Chem. Commun. 2017, 53, 5481.
7. [7]
8. [8]
  Duret, G.; Quinlan, R.; Bisseret, P.; Blanchard, N. Chem. Sci. 2015, 6, 5366. doi: 10.1039/C5SC02207J
9. [9]
  Duan, K.; Yan, X.; Liu, Y.; Li, Z. Adv. Synth. Catal. 2018, 360, 2781. doi: 10.1002/adsc.201701626
10. [10]
  Huang, H.; Zhang, G.; Gong, L.; Zhang, S.; Chen, Y. J. Am. Chem. Soc. 2014, 136, 2280. doi: 10.1021/ja413208y
11. [11]
  Dai, J. J.; Zhang, W. M.; Shu, Y. J.; Sun, Y. Y.; Xu, J.; Feng, Y. S.; Xu, H. J. Chem. Commun. 2016, 52, 6793. doi: 10.1039/C6CC01530A
12. [12]
  Heitz, D. R.; Rizwan, K.; Molander, G. A. J. Org. Chem. 2016, 81, 7308. doi: 10.1021/acs.joc.6b01207
13. [13]
  Shi, D.; Xia, C.; Liu, C. CCS Chem. 2020, 2, 1718.
14. [14]
  Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
15. [15]
  Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896. doi: 10.1021/ja513079r
16. [16]
  Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2015, 137, 2195. doi: 10.1021/ja512946e
17. [17]
  Primer, D. N.; Molander, G. A. J. Am. Chem. Soc. 2017, 139, 9847. doi: 10.1021/jacs.7b06288
18. [18]
  Alam, R.; Molander, G. A. J. Org. Chem. 2017, 82, 13728. doi: 10.1021/acs.joc.7b02589
19. [19]
  Ryu, D.; Primer, D. N.; Tellis, J. C.; Molander, G. A. Chem.-Eur. J. 2016, 22, 120. doi: 10.1002/chem.201504079
20. [20]
  Tellis, J. C.; Amani, J.; Molander, G. A. Org. Lett. 2016, 18, 2994. doi: 10.1021/acs.orglett.6b01357
21. [21]
  Matsui, J. K.; Molander, G. A. Org. Lett. 2017, 19, 436. doi: 10.1021/acs.orglett.6b03448
22. [22]
  Lima, F.; Kabeshov, M. A.; Tran, D. N.; Battilocchio, C.; Sedelmeier, J.; Sedelmeier, G.; Schenkel, B.; Ley, S. V. Angew. Chem., Int. Ed. 2016, 55, 14085. doi: 10.1002/anie.201605548
23. [23]
  Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Tetrahedron 1971, 27, 3575. doi: 10.1016/S0040-4020(01)97768-3
24. [24]
  Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int.Ed. 2019, 58, 13666. doi: 10.1002/anie.201900977
25. [25]
  Li, G. X.; Morales-Rivera, C. A.; Wang, Y. X.; Gao, F.; He, G.; Liu, P.; Chen, G. Chem. Sci. 2016, 7, 6407. doi: 10.1039/C6SC02653B
26. [26]
  Zhang, W. M.; Dai, J. J.; Xu, J.; Xu, H. J. J. Org. Chem. 2017, 82, 2059. doi: 10.1021/acs.joc.6b02891
27. [27]
  Matsui, J. K.; Primer, D. N.; Molander, G. A. Chem. Sci. 2017, 8, 3512. doi: 10.1039/C7SC00283A
28. [28]
  Yan, H.; Hou, Z. W.; Xu, H. C. Angew. Chem., Int. Ed. 2019, 58, 4592. doi: 10.1002/anie.201814488
29. [29]
  Amani, J.; Sodagar, E.; Molander, G. A. Org. Lett. 2016, 18, 732. doi: 10.1021/acs.orglett.5b03705
30. [30]
  Amani, J.; Molander, G. A. J. Org. Chem. 2017, 82, 1856. doi: 10.1021/acs.joc.6b02897
31. [31]
  Amani, J.; Alam, R.; Badir, S.; Molander, G. A. Org. Lett. 2017, 19, 2426. doi: 10.1021/acs.orglett.7b00989
32. [32]
  Amani, J.; Molander, G. A. Org. Lett. 2017, 19, 3612. doi: 10.1021/acs.orglett.7b01588
33. [33]
  Stache, E. E.; Rovis, T.; Doyle, A. G. Angew. Chem., Int. Ed. 2017, 56, 3679. doi: 10.1002/anie.201700097
34. [34]
  Liu, W.; Liu, P.; Lv, L.; Li, C. J. Angew. Chem., Int. Ed. 2018, 57, 13499. doi: 10.1002/anie.201807181
35. [35]
  Huang, H.; Jia, K.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 1881. doi: 10.1002/anie.201410176
36. [36]
  Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. Chem. Commun. 2013, 49, 7249. doi: 10.1039/c3cc42695e
37. [37]
  Miyazawa, K.; Koike, T.; Akita, M. Adv. Synth. Catal. 2014, 356, 2749. doi: 10.1002/adsc.201400556
38. [38]
  Li, Y.; Miyazawa, K.; Koike, T.; Akita, M. Org. Chem. Front. 2015, 2, 319. doi: 10.1039/C4QO00352G
39. [39]
  Chinzei, T.; Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. RSC Adv. 2015, 5, 21297. doi: 10.1039/C5RA01826A
40. [40]
  Iwata, Y.; Tanaka, Y.; Kubosaki, S.; Morita, T.; Yoshimi, Y. Chem. Commun. 2018, 54, 1257. doi: 10.1039/C7CC09140K
41. [41]
  Lang, S. B.; Wiles, R. J.; Kelly, C. B.; Molander, G. A. Angew. Chem., Int. Ed. 2017, 56, 15073. doi: 10.1002/anie.201709487
42. [42]
  Huo, H.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2016, 138, 6936. doi: 10.1021/jacs.6b03399
43. [43]
  Tutkowski, B.; Meggers, E.; Wiest, O. J. Am. Chem. Soc. 2017, 139, 8062. doi: 10.1021/jacs.7b01786
44. [44]
  Plasko, D. P.; Jordan, C. J.; Ciesa, B. E.; Merrill, M. A.; Hanna, J. M. Photochem. Photobiol. Sci. 2018, 17, 534. doi: 10.1039/C8PP00061A
45. [45]
  Yi, J.; Badir, S. O.; Alam, R.; Molander, G. A. Org. Lett. 2019, 21, 4853. doi: 10.1021/acs.orglett.9b01747
46. [46]
  Yu, X. Y.; Zhou, Q. Q.; Wang, P. Z.; Liao, C. M.; Chen, J. R.; Xiao, W. J. Org. Lett. 2018, 20, 421. doi: 10.1021/acs.orglett.7b03747
47. [47]
  Liu, M.; Huang, H.; Chen, Y. Chin. J. Chem. 2018, 36, 1209. doi: 10.1002/cjoc.201800461
48. [48]
  Xie, S.; Li, D.; Huang, H.; Zhang, F.; Chen, Y. J. Am. Chem. Soc. 2019, 141, 16237. doi: 10.1021/jacs.9b09099
49. [49]
  Li, X.; Han, M.-Y.; Wang, B.; Wang, L.; Wang, M. Org. Biomol. Chem. 2019, 17, 6612. doi: 10.1039/C9OB01023H
50. [50]
  Sim, J.; Campbell, M. W.; Molander, G. A. ACS Catal. 2019, 9, 1558. doi: 10.1021/acscatal.8b04284
51. [51]
  Campbell, M. W.; Compton, J. S.; Kelly, C. B.; Molander, G. A. J. Am. Chem. Soc. 2019, 141, 20069. doi: 10.1021/jacs.9b08282
52. [52]
  Lima, F.; Sharma, U. K.; Grunenberg, L.; Saha, D.; Johannsen, S.; Sedelmeier, J.; Van der Eycken, E. V.; Ley, S. V. Angew. Chem., Int. Ed. 2017, 56, 15136. doi: 10.1002/anie.201709690
53. [53]
  Lima, F.; Grunenberg, L.; Rahman, H. B. A.; Labes, R.; Sedelmeier, J.; Ley, S. V. Chem. Commun. 2018, 54, 5606. doi: 10.1039/C8CC02169D
54. [54]
  Chen, Y.; May, O.; Blakemore, D. C.; Ley, S. V. Org. Lett. 2019, 21, 6140. doi: 10.1021/acs.orglett.9b02307
55. [55]
  Ye, H.; Ye, Q.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2018, 59, 2046. doi: 10.1016/j.tetlet.2018.04.035
56. [56]
  Ye, H.; Zhao, H.; Ren, S.; Ye, H.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2019, 60, 1302. doi: 10.1016/j.tetlet.2019.04.015
57. [57]
  Shu, C.; Noble, A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2019, 58, 3870. doi: 10.1002/anie.201813917
58. [58]
  Kaiser, D.; Noble, A.; Fasano, V.; Aggarwal, V. K. J. Am. Chem. Soc. 2019, 141, 14104. doi: 10.1021/jacs.9b07564
59. [59]
  Yasu, Y.; Koike, T.; Akita, M. Adv. Synth. Catal. 2012, 354, 3414. doi: 10.1002/adsc.201200588
60. [60]
  Zou, Y. Q.; Chen, J. R.; Liu, X. P.; Lu, L. Q.; Davis, R. L.; Jorgensen, K. A.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 784. doi: 10.1002/anie.201107028
61. [61]
  Weng, W. Z.; Liang, H.; Zhang, B. Org. Lett. 2018, 20, 4979. doi: 10.1021/acs.orglett.8b02095
62. [62]
  Liu, T.; Li, Y.; Lai, L.; Cheng, J.; Sun, J.; Wu, J. Org. Lett. 2018, 20, 3605. doi: 10.1021/acs.orglett.8b01385
63. [63]
  Ye, S.; Li, X.; Xie, W.; Wu, J. Asian J. Org. Chem. 2019, 8, 893. doi: 10.1002/ajoc.201900172
64. [64]
  Liu, T.; Ding, Y.; Fan, X.; Wu, J. Org. Chem. Front. 2018, 5, 3153. doi: 10.1039/C8QO00965A
65. [65]
  Gong, X.; Yang, M.; Liu, J.-B.; He, F.-S.; Wu, J. Org. Chem. Front. 2020, 7, 938.
66. [66]
  Clausen, F.; Kischkewitz, M.; Bergander, K.; Studer, A. Chem. Sci. 2019, 10, 6210. doi: 10.1039/C9SC02067E
1. [1]
  Qin Hu , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Ni掺杂构建电子桥及激活MoS₂惰性基面增强光催化分解水产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2406024-. doi: 10.3866/PKU.WHXB202406024
2. [2]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
3. [3]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
4. [4]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
5. [5]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
6. [6]
  Jiajie Cai , Chang Cheng , Bowen Liu , Jianjun Zhang , Chuanjia Jiang , Bei Cheng . CdS/DBTSO-BDTO S型异质结光催化制氢及其电荷转移动力学. Acta Physico-Chimica Sinica, 2025, 41(8): 100084-. doi: 10.1016/j.actphy.2025.100084
7. [7]
  Yu Wang , Haiyang Shi , Zihan Chen , Feng Chen , Ping Wang , Xuefei Wang . 具有富电子Pt^δ^-壳层的空心AgPt@Pt核壳催化剂：提升光催化H₂O₂生成选择性与活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-. doi: 10.1016/j.actphy.2025.100081
8. [8]
  Yuchen Zhou , Huanmin Liu , Hongxing Li , Xinyu Song , Yonghua Tang , Peng Zhou . Designing thermodynamically stable noble metal single-atom photocatalysts for highly efficient non-oxidative conversion of ethanol into high-purity hydrogen and value-added acetaldehyde. Acta Physico-Chimica Sinica, 2025, 41(6): 100067-. doi: 10.1016/j.actphy.2025.100067
9. [9]
  Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H₂O and Its Intermediates on Electron-Deficient Mn^(3+δ)+ for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
10. [10]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
11. [11]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
12. [12]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
13. [13]
  Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . ZnCoP/CdLa₂S₄肖特基异质结的构建促进光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-. doi: 10.3866/PKU.WHXB202404030
14. [14]
  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
15. [15]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
16. [16]
  Zijian Jiang , Yuang Liu , Yijian Zong , Yong Fan , Wanchun Zhu , Yupeng Guo . Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity. University Chemistry, 2024, 39(5): 266-273. doi: 10.3866/PKU.DXHX202311101
17. [17]
  Xia ZHANG , Yushi BAI , Xi CHANG , Han ZHANG , Haoyu ZHANG , Liman PENG , Shushu HUANG . Preparation and photocatalytic degradation performance of rhodamine B of BiOCl/polyaniline. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 913-922. doi: 10.11862/CJIC.20240255
18. [18]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
19. [19]
  Jingyu Cai , Xiaoyu Miao , Yulai Zhao , Longqiang Xiao . Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol. University Chemistry, 2024, 39(4): 169-177. doi: 10.3866/PKU.DXHX202311028
20. [20]
  Yulian Hu , Xin Zhou , Xiaojun Han . A Virtual Simulation Experiment on the Design and Property Analysis of CO₂ Reduction Photocatalyst. University Chemistry, 2025, 40(3): 30-35. doi: 10.12461/PKU.DXHX202403088

Get Citation

PDF

XML

Metrics

PDF Downloads(83)
Abstract views(4595)
HTML views(946)

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