Citation: Zhu Wenming, Ying Weiwei, Wei Wenting. Progress in Carbon-Oxygen Bonds Formation Using tert-Butyl Hydroperoxide[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2841-2849. doi: 10.6023/cjoc201706005 shu

Progress in Carbon-Oxygen Bonds Formation Using tert-Butyl Hydroperoxide

School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211

Corresponding author: Wei Wenting, weiwenting@nbu.edu.cn

Received Date: 4 June 2017
Revised Date: 2 July 2017
Available Online: 14 November 2017
Fund Project: Project supported by the Research Funds of Ningbo University (No. ZX2016000706), the Foundation of Ningbo University (No. XYL17009) and the K. C. Wong Magna Fund in Ningbo Universitythe Foundation of Ningbo University XYL17009the Research Funds of Ningbo University ZX2016000706

Figures(7)

The formation of carbon-oxygen bonds is one of the hot topics in the field of organic synthesis methodology. Recently, the remarkable progress has been made in construction of carbon-oxygen bonds using tert-butyl hydroperoxide in radical reactions. The present protocol, which utilizes tert-butyl hydroperoxide as oxidant and oxygen source, provides a green and atom economy approach to ketones, esters and alcohols etc. This review will summarize the recent development in this area on the basis of different chemical bonds.
- tert-butyl hydroperoxide,
- carbon-oxygen bond,
- radical reaction
1. [1]
  Turner, N. J. Chem. Rev. 2011, 111, 4073. doi: 10.1021/cr200111v
2. [2]
  Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318. doi: 10.1021/cr068006f
3. [3]
  Liu, A.-S.; Wang, X.-G.; Ou, X.-M.; Liu, S.-D.; Mo, H.-B.; Liu, X.-P.; Wang, T.-J.; He, H.-J.; Hu, L.; Huang, M.-Z.; Liu, Z.-J.; Yao, J.-R. Chin. J. Org. Chem. 2008, 28, 1772 (in Chinese).
4. [4]
  Shang, X.-J.; Liu, Z.-Q. Acta Chim. Sinica 2015, 73, 1275 (in Chinese).
5. [5]
  Lu, Q.-Q.; Yi, H.; Lei, A. W. Acta Chim. Sinica 2015, 73, 1245 (in Chinese). doi: 10.3969/j.issn.0253-2409.2015.10.013
6. [6]
  Liu, Y.; Liu, Z.; Cui, Y. D. Chin. J. Chem. 2015, 33, 175. doi: 10.1002/cjoc.v33.2
7. [7]
  Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369. doi: 10.1021/ja990324r
8. [8]
  Gowrisankar, S.; Sergeev, A. G.; Anbarasan, P.; Spannenberg, A.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 11592. doi: 10.1021/ja103248d
9. [9]
  Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. doi: 10.1021/ja962408v
10. [10]
  Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. doi: 10.1002/(ISSN)1521-3773
11. [11]
  Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954. doi: 10.1002/anie.v48:38
12. [12]
  Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770. doi: 10.1021/ja016863p
13. [13]
  Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043. doi: 10.1021/ja000094c
14. [14]
  Niu, J.; Guo, P.; Kang, J.; Li, Z.; Xu, J.; Hu, S. J. Org. Chem. 2009, 74, 5075. doi: 10.1021/jo900600m
15. [15]
  Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790. doi: 10.1021/ja061715q
16. [16]
  Jiang, T. S.; Wang, G. W. J. Org. Chem. 2012, 77, 9504. doi: 10.1021/jo301964m
17. [17]
  Yin, Z.-W.; Jiang, X.-Q.; Sun, P.-P. J. Org. Chem. 2013, 78, 10002. doi: 10.1021/jo401623j
18. [18]
  Shi, S.-P.; Kuang, C.-X. J. Org. Chem. 2014, 79, 6105. doi: 10.1021/jo5008306
19. [19]
  Xie, Y.-X.; Song, R.-J.; Xiang, J.-N.; Li, J.-H. Chin. J. Org. Chem. 2012, 32, 1555 (in Chinese).
20. [20]
  He, H.; Pei, B.-J.; Lee, A. W. M. Green Chem. 2009, 11, 1857. doi: 10.1039/b916265h
21. [21]
  Yin, Z.-W.; Sun, P.-P. J. Org. Chem. 2012, 77, 11339. doi: 10.1021/jo302125h
22. [22]
  Ali, W.; Behera, A.; Guin, S.; Patel, B. K. J. Org. Chem. 2015, 80, 5625. doi: 10.1021/acs.joc.5b00501
23. [23]
  Khemnar, A. B.; Bhanage, B. M. Org. Biomol. Chem. 2015, 46, 9631.
24. [24]
  Khatun, N.; Banerjee, A.; Santra, S. K.; Ali, W.; Patel, B. K. RSC Adv. 2015, 5, 36461. doi: 10.1039/C5RA03462K
25. [25]
  Chen, X.-L.; Li, Y.; Wu, M.-H.; Guo, H.-B.; Jiang, L.-Q.; Wang, J.; Sun, S.-F. RSC Adv. 2016, 6, 102023. doi: 10.1039/C6RA20966A
26. [26]
  Hashemi, H.; Saberi, D.; Poorsadeghic, S.; Niknam, K. RSC Adv. 2017, 7, 7619. doi: 10.1039/C6RA27921J
27. [27]
  Tan, J.-J.; Zheng, T.-Y.; Yu, Y.-Q.; Xu, K. RSC Adv. 2017, 7, 15176. doi: 10.1039/C7RA00352H
28. [28]
  Zhang, X.-B.; Wang, L. Green Chem. 2012, 14, 2141. doi: 10.1039/c2gc35489f
29. [29]
  Zhao, Q.; Miao, T.; Zhang, X. B.; Zhou, W.; Wang, L. Org. Biomol. Chem. 2013, 11, 1867. doi: 10.1039/c3ob27433k
30. [30]
  Zhang, X. B.; Wang, M.; Zhang, Y. C.; Wang, L. RSC Adv. 2013, 3, 1311. doi: 10.1039/C2RA22116K
31. [31]
  Behera, A.; Ali, W.; Tripathy, M.; Sahoo, D.; Patel, B. K. RSC Adv. 2016, 6, 91308. doi: 10.1039/C6RA16118A
32. [32]
  Majji, G.; Rajamanickam, S.; Khatun, N.; Santra, S.-K.; Patel, B. K. J. Org. Chem. 2015, 80, 3440. doi: 10.1021/jo502903d
33. [33]
  Wang, Q.-Q.; Wang, Z.-X.; Xu, Y.-S.; Zhang, X.-Y.; Fan, X.-S. Asian J. Org. Chem. 2016, 5, 1304. doi: 10.1002/ajoc.v5.11
34. [34]
  Majji, G.; Guin, S.; Gogoi, A.; Rout, S. K.; Pate, B. K. Chem. Commun. 2013, 49, 3031. doi: 10.1039/c3cc40832a
35. [35]
  Du, B.; Jina, B.; Sun, P.-P. Org. Biomol. Chem. 2014, 12, 4586. doi: 10.1039/C4OB00520A
36. [36]
  Zhao, J.-C.; Fang, H.; Han, J.; Pan, Yi. Org. Lett. 2014, 16, 2530. doi: 10.1021/ol5009119
37. [37]
  Guo, S.-J.; Yu, J.-T.; Dai, Q.; Yang, H.-T.; Cheng, J. Chem. Commun. 2014, 50, 6240. doi: 10.1039/c4cc01652a
38. [38]
  Azizi, K.; Karim, M.; Heydari, A. RSC Adv. 2014, 4, 31817. doi: 10.1039/C4RA04215H
39. [39]
  Liu, F.-Y.; Zhang, K.; Liu, Y.-F.; Chen, S.; Chen, Y.-P.; Zhang, D.-L.; Lin, C.-F.; Wang, B. RSC Adv. 2017, 7, 7158. doi: 10.1039/C6RA26679G
40. [40]
  Xu, J.-N.; Song, Q.-L. Chin. J. Org. Chem. 2016, 36, 1151 (in Chinese).
41. [41]
  Jiang, H.-F.; Huang, H.-W.; Cao, H.; Qi, C.-R. Org. Lett. 2010, 12, 5561. doi: 10.1021/ol1023085
42. [42]
  Belala, M.; Khan, A. T. RSC Adv. 2016, 6, 18891. doi: 10.1039/C5RA27993C
43. [43]
  Khatun, N.; Banerjee, A.; Santra, S. K.; Behera, A.; Patel, B. K. RSC Adv. 2014, 4, 54532. doi: 10.1039/C4RA11014E
44. [44]
  Wei, W.-T.; Yang, X.-H.; Li, H.-B.; Li, J.-H. Adv. Synth. Catal. 2015, 357, 59. doi: 10.1002/adsc.v357.1
45. [45]
  Wei, W.; Zhang, C.; Xu, Y.; Wan, X. B. Chem. Commun. 2011, 47, 10827. doi: 10.1039/c1cc14602e
46. [46]
  Yang, X.-H.; Wei, W.-T.; Li, H.-B.; Song, R.-J.; Li, J.-H. Chem. Commun. 2014, 50, 12867. doi: 10.1039/C4CC05051G
47. [47]
  Yang, W.-C.; Weng, S.-S.; Ramasamy, A.; Rajeshwaren, G.; Liao, Y.-Y.; Chen, C.-T. Org. Biomol. Chem. 2015, 13, 2385. doi: 10.1039/C4OB02621G
48. [48]
  Lan, X.-W.; Wang, N.-X.; Zhang, W.; Wen, J.-L.; Bai, C.-B.; Xing, Y.-L.; Li, Y.-H. Org. Lett. 2015, 17, 4460. doi: 10.1021/acs.orglett.5b02116
49. [49]
  Wei, W.-T.; Li, H.-B.; Song, R.-J.; Li, J.-H. Chem. Commun. 2015, 51, 11325. doi: 10.1039/C5CC03468J
50. [50]
  Jiang, J.-W.; Liu, J.-J.; Yang, L.; Shao, Y.; Cheng, J.; Bao, X.-G.; Wan, X.-B. Chem. Commun. 2015, 51, 14728. doi: 10.1039/C5CC05183E
51. [51]
  Banerjee, A.; Santra, S. K.; Khatun, N.; Ali, W.; Patel, B. K. Chem. Commun. 2015, 51, 15422. doi: 10.1039/C5CC06200D
52. [52]
  Yi, N.-N.; Zhang, H.; Xu, C.-H.; Deng, W.; Wang, R.-J.; Peng, D.-M.; Zeng, Z.-B.; Xiang, J.-J. Org. Lett. 2016, 18, 1780. doi: 10.1021/acs.orglett.6b00498
53. [53]
  Shi, E.; Liu, J. J.; Liu, C. M.; Shao, Y.; Wang, H. H.; Lv, Y. Z.; Ji, M. S.; Bao, X. G.; Wan, X. B. J. Org. Chem. 2016, 81, 5878. doi: 10.1021/acs.joc.6b00575
54. [54]
  Du, P.; Li, H.-H.; Wang, Y.-X.; Cheng, J.; Wan, X.-B. Org. Lett. 2014, 16, 6350. doi: 10.1021/ol503128j
55. [55]
  Zhang, J.; Jiang, J. W.; Xu, D. M.; Luo, Q.; Wang, H. X.; Chen, J. J.; Li, H. H.; Wang, Y. X.; Wan, X. B. Angew. Chem., Int. Ed. 2015, 54, 1231. doi: 10.1002/anie.201408874
56. [56]
  Ling, J.-Y.; Zhang, J.; Zhao, Y.-W.; Xu, Y.-D.; Wang, H.-H.; Lv, Y.-Z.; Ji, M.-S.; Ma, L.; Maa, M.-H.; Wan, X.-B. Org. Biomol. Chem. 2016, 14, 5310. doi: 10.1039/C6OB00873A
57. [57]
  Liu, C. M.; Shi, E.; Xu, F.; Luo, Q.; Wang, H. X.; Chen, J. J.; Wan, X. B. Chem. Commun. 2015, 51, 1214. doi: 10.1039/C4CC07833K
58. [58]
  Luo, Q.; Liu, C. M.; Tong, J. J.; Shao, Y.; Shan, W. Y.; Wang, H. H.; Zheng, H.; Cheng, J.; Wan, X. B. J. Org. Chem. 2016, 81, 3103. doi: 10.1021/acs.joc.5b02664
59. [59]
  Ratnikov, M. O.; Farkas, L. E.; McLaughlin, E. C.; Chiou, G.; Choi, H.; El-Khalafy, S. H.; Doyle, M. P. J. Org. Chem. 2011, 76, 2585. doi: 10.1021/jo1024865
60. [60]
  Dong, J.-W.; Liu, P.; Sun, P.-P. J. Org. Chem. 2015, 80, 2925. doi: 10.1021/acs.joc.5b00167
61. [61]
  Duan, S.-T.; Xu, Y.-S.; Zhang, X.-Y.; Fan, X.-S. Chem. Commun. 2016, 52, 10529. doi: 10.1039/C6CC04756D
62. [62]
  Dang, P.; Zheng, Z.-L.; Liang, Y. J. Org. Chem. 2017, 82, 2263. doi: 10.1021/acs.joc.6b02943
63. [63]
  Chen, X.; Tan, Z.; Gui, Q.-W.; Hu, L.; Liu, J.-D.; Wu, J.; Wang, G.-W. Chem. Eur. J. 2016, 22, 6218. doi: 10.1002/chem.v22.18
64. [64]
  Zi, Y.; Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2014, 16, 3094. doi: 10.1021/ol501203q
65. [65]
  Yan, K.-L.; Yang, D.-S.; Wei, W.; Li, G.-Q.; Sun, M.-Y.; Zhang, Q.-Y.; Tian, L.-J.; Wang, H. RSC Adv. 2015, 5, 100102. doi: 10.1039/C5RA17740E
66. [66]
  Luo, W.-K.; Shi, X.; Zhou, W.; Yang, L. Org. Lett. 2016, 18, 2036. doi: 10.1021/acs.orglett.6b00646
67. [67]
  Kong, L.-K.; Wang, M.-D.; Zhang, F.-F.; Xu, M.-R.; Li, Y.-Z. Org. Lett. 2016, 18, 6124. doi: 10.1021/acs.orglett.6b03131
68. [68]
  Zhang, J.; Lu, Q.-Q.; Liu, C.; Lei, A. Chin. J. Org. Chem. 2015, 35, 743 (in Chinese).
69. [69]
  Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Niu, Y.-N.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 1410. doi: 10.1039/c2cc37805a
70. [70]
  Gogoi, A.; Modi, A.; Guin, S.; Rout, S. K.; Das, D.; Patel, B. K. Chem. Commun. 2014, 50, 10445. doi: 10.1039/C4CC04407J
71. [71]
  Rout, S. K.; Guin, S.; Gogoi, A.; Majji, G.; Patel, B. K. Org. Lett. 2014, 16, 1614. doi: 10.1021/ol500224e
72. [72]
  Zhang, P.-B.; Zhang, L.-L.; Gao, Y.-Z.; Xu, J.; Fang, H.; Tang, G.; Zhao, Y.-F. Chem. Commun. 2015, 51, 7839. doi: 10.1039/C5CC01904D
73. [73]
  Li, Y.-J.; Yan, N.; Liu, C.-H.; Yu, Y.; Zhao, Y.-L. Org. Lett. 2017, 19, 1160. doi: 10.1021/acs.orglett.7b00200
1. [1]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
2. [2]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
3. [3]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
4. [4]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
5. [5]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
6. [6]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
7. [7]
  Yuan GAO , Yiming LIU , Chunhui WANG , Zhe HAN , Chaoyue FAN , Jie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271
8. [8]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
9. [9]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
10. [10]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
11. [11]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
12. [12]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
13. [13]
  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
14. [14]
  Xinxin Wu . 基础有机化学教学中自由基重排反应的课程设计及其课程思政元素的融入. University Chemistry, 2025, 40(6): 316-325. doi: 10.12461/PKU.DXHX202408055
15. [15]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
16. [16]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
17. [17]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
18. [18]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
19. [19]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
20. [20]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049

Get Citation

PDF

XML

Metrics

PDF Downloads(75)
Abstract views(10597)
HTML views(1474)

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