Reviews

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

  • Zhu Wenming ,
  • Ying Weiwei ,
  • Wei Wenting
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  • School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211

Received date: 2017-06-04

  Revised date: 2017-07-02

  Online published: 2017-07-14

Supported by

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 University.

Abstract

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.

Cite this article

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

References

[1] Turner, N. J. Chem. Rev. 2011, 111, 4073.
[2] Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
[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). (柳爱平, 王晓光, 欧晓明, 刘曙东, 莫洪波, 刘兴平, 王婷瑾, 何海军, 胡礼, 黄明智, 刘钊杰, 姚建仁, 有机化学, 2008, 28, 1772.)
[4] Shang, X.-J.; Liu, Z.-Q. Acta Chim. Sinica 2015, 73, 1275(in Chinese). (尚筱洁, 柳忠全, 化学学报, 2015, 73, 1275.)
[5] Lu, Q.-Q.; Yi, H.; Lei, A. W. Acta Chim. Sinica 2015, 73, 1245(in Chinese). (陆庆全, 易红, 雷爱文, 化学学报, 2015, 73, 1245.)
[6] Liu, Y.; Liu, Z.; Cui, Y. D. Chin. J. Chem. 2015, 33, 175.
[7] Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
[8] Gowrisankar, S.; Sergeev, A. G.; Anbarasan, P.; Spannenberg, A.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 11592.
[9] Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
[10] Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
[11] Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954.
[12] Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770.
[13] Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
[14] Niu, J.; Guo, P.; Kang, J.; Li, Z.; Xu, J.; Hu, S. J. Org. Chem. 2009, 74, 5075.
[15] Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
[16] Jiang, T. S.; Wang, G. W. J. Org. Chem. 2012, 77, 9504.
[17] Yin, Z.-W.; Jiang, X.-Q.; Sun, P.-P. J. Org. Chem. 2013, 78, 10002.
[18] Shi, S.-P.; Kuang, C.-X. J. Org. Chem. 2014, 79, 6105.
[19] Xie, Y.-X.; Song, R.-J.; Xiang, J.-N.; Li, J.-H. Chin. J. Org. Chem. 2012, 32, 1555(in Chinese). (谢叶香, 宋仁杰, 向建南, 李金恒, 有机化学, 2012, 32, 1555.)
[20] He, H.; Pei, B.-J.; Lee, A. W. M. Green Chem. 2009, 11, 1857.
[21] Yin, Z.-W.; Sun, P.-P. J. Org. Chem. 2012, 77, 11339.
[22] Ali, W.; Behera, A.; Guin, S.; Patel, B. K. J. Org. Chem. 2015, 80, 5625.
[23] Khemnar, A. B.; Bhanage, B. M. Org. Biomol. Chem. 2015, 46, 9631.
[24] Khatun, N.; Banerjee, A.; Santra, S. K.; Ali, W.; Patel, B. K. RSC Adv. 2015, 5, 36461.
[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.
[26] Hashemi, H.; Saberi, D.; Poorsadeghic, S.; Niknam, K. RSC Adv. 2017, 7, 7619.
[27] Tan, J.-J.; Zheng, T.-Y.; Yu, Y.-Q.; Xu, K. RSC Adv. 2017, 7, 15176.
[28] Zhang, X.-B.; Wang, L. Green Chem. 2012, 14, 2141.
[29] Zhao, Q.; Miao, T.; Zhang, X. B.; Zhou, W.; Wang, L. Org. Biomol. Chem. 2013, 11, 1867.
[30] Zhang, X. B.; Wang, M.; Zhang, Y. C.; Wang, L. RSC Adv. 2013, 3, 1311.
[31] Behera, A.; Ali, W.; Tripathy, M.; Sahoo, D.; Patel, B. K. RSC Adv. 2016, 6, 91308.
[32] Majji, G.; Rajamanickam, S.; Khatun, N.; Santra, S.-K.; Patel, B. K. J. Org. Chem. 2015, 80, 3440.
[33] Wang, Q.-Q.; Wang, Z.-X.; Xu, Y.-S.; Zhang, X.-Y.; Fan, X.-S. Asian J. Org. Chem. 2016, 5, 1304.
[34] Majji, G.; Guin, S.; Gogoi, A.; Rout, S. K.; Pate, B. K. Chem. Commun. 2013, 49, 3031.
[35] Du, B.; Jina, B.; Sun, P.-P. Org. Biomol. Chem. 2014, 12, 4586.
[36] Zhao, J.-C.; Fang, H.; Han, J.; Pan, Yi. Org. Lett. 2014, 16, 2530.
[37] Guo, S.-J.; Yu, J.-T.; Dai, Q.; Yang, H.-T.; Cheng, J. Chem. Commun. 2014, 50, 6240.
[38] Azizi, K.; Karim, M.; Heydari, A. RSC Adv. 2014, 4, 31817.
[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.
[40] Xu, J.-N.; Song, Q.-L. Chin. J. Org. Chem. 2016, 36, 1151(in Chinese). (许健, 宋秋玲, 有机化学, 2016, 36, 1151.)
[41] Jiang, H.-F.; Huang, H.-W.; Cao, H.; Qi, C.-R. Org. Lett. 2010, 12, 5561.
[42] Belala, M.; Khan, A. T. RSC Adv. 2016, 6, 18891.
[43] Khatun, N.; Banerjee, A.; Santra, S. K.; Behera, A.; Patel, B. K. RSC Adv. 2014, 4, 54532.
[44] Wei, W.-T.; Yang, X.-H.; Li, H.-B.; Li, J.-H. Adv. Synth. Catal. 2015, 357, 59.
[45] Wei, W.; Zhang, C.; Xu, Y.; Wan, X. B. Chem. Commun. 2011, 47, 10827.
[46] Yang, X.-H.; Wei, W.-T.; Li, H.-B.; Song, R.-J.; Li, J.-H. Chem. Commun. 2014, 50, 12867.
[47] Yang, W.-C.; Weng, S.-S.; Ramasamy, A.; Rajeshwaren, G.; Liao, Y.-Y.; Chen, C.-T. Org. Biomol. Chem. 2015, 13, 2385.
[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.
[49] Wei, W.-T.; Li, H.-B.; Song, R.-J.; Li, J.-H. Chem. Commun. 2015, 51, 11325.
[50] Jiang, J.-W.; Liu, J.-J.; Yang, L.; Shao, Y.; Cheng, J.; Bao, X.-G.; Wan, X.-B. Chem. Commun. 2015, 51, 14728.
[51] Banerjee, A.; Santra, S. K.; Khatun, N.; Ali, W.; Patel, B. K. Chem. Commun. 2015, 51, 15422.
[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.
[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.
[54] Du, P.; Li, H.-H.; Wang, Y.-X.; Cheng, J.; Wan, X.-B. Org. Lett. 2014, 16, 6350.
[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.
[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.
[57] Liu, C. M.; Shi, E.; Xu, F.; Luo, Q.; Wang, H. X.; Chen, J. J.; Wan, X. B. Chem. Commun. 2015, 51, 1214.
[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.
[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.
[60] Dong, J.-W.; Liu, P.; Sun, P.-P. J. Org. Chem. 2015, 80, 2925.
[61] Duan, S.-T.; Xu, Y.-S.; Zhang, X.-Y.; Fan, X.-S. Chem. Commun. 2016, 52, 10529.
[62] Dang, P.; Zheng, Z.-L.; Liang, Y. J. Org. Chem. 2017, 82, 2263.
[63] Chen, X.; Tan, Z.; Gui, Q.-W.; Hu, L.; Liu, J.-D.; Wu, J.; Wang, G.-W. Chem. Eur. J. 2016, 22, 6218.
[64] Zi, Y.; Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2014, 16, 3094.
[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.
[66] Luo, W.-K.; Shi, X.; Zhou, W.; Yang, L. Org. Lett. 2016, 18, 2036.
[67] Kong, L.-K.; Wang, M.-D.; Zhang, F.-F.; Xu, M.-R.; Li, Y.-Z. Org. Lett. 2016, 18, 6124.
[68] Zhang, J.; Lu, Q.-Q.; Liu, C.; Lei, A. Chin. J. Org. Chem. 2015, 35, 743(in Chinese). (张剑, 陆庆全, 刘超, 雷爱文, 有机化学, 2015, 35, 743.)
[69] Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Niu, Y.-N.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 1410.
[70] Gogoi, A.; Modi, A.; Guin, S.; Rout, S. K.; Das, D.; Patel, B. K. Chem. Commun. 2014, 50, 10445.
[71] Rout, S. K.; Guin, S.; Gogoi, A.; Majji, G.; Patel, B. K. Org. Lett. 2014, 16, 1614.
[72] Zhang, P.-B.; Zhang, L.-L.; Gao, Y.-Z.; Xu, J.; Fang, H.; Tang, G.; Zhao, Y.-F. Chem. Commun. 2015, 51, 7839.
[73] Li, Y.-J.; Yan, N.; Liu, C.-H.; Yu, Y.; Zhao, Y.-L. Org. Lett. 2017, 19, 1160.

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