Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 129-146.DOI: 10.6023/cjoc202107032 Previous Articles Next Articles
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收稿日期:
2021-07-15
修回日期:
2021-08-15
发布日期:
2021-09-02
通讯作者:
邓国军
基金资助:
Shuowen Wang, Pingyu Jiang, Rong Li, Muyang Yang, Guojun Deng()
Received:
2021-07-15
Revised:
2021-08-15
Published:
2021-09-02
Contact:
Guojun Deng
Supported by:
Share
Shuowen Wang, Pingyu Jiang, Rong Li, Muyang Yang, Guojun Deng. Progress in Selective Construction of Functional Aromatics with Cyclohexanone[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 129-146.
[1] |
Lin, C.-J.; Huang, S.-H.; Lai, N.-C.; Yang, C.-M. ACS Catal. 2015, 5, 4121.
doi: 10.1021/acscatal.5b00380 |
[2] |
Liu, T. Z.; Zhou, H.; Han, B. B.; Gu, Y. B.; Li, S. Q.; Zheng, J.; Zhong, X.; Zhuang, G.-L.; Wang, J.-G. ACS Sustainable Chem. Eng. 2017, 5, 11628.
doi: 10.1021/acssuschemeng.7b02974 |
[3] |
Wang, Y.; Zhang, J. S.; Wang, X. C.; Antonietti, M.; Li, H. R. Angew. Chem., Int. Ed. 2010, 49, 3356.
doi: 10.1002/anie.201000120 |
[4] |
Wang, W.; Liu, J. J.; Zhang, L. Chem. Ind. Eng. Prog. 2013, 32, 2156. (in Chinese)
|
(王巍, 刘晶晶, 张龙, 化工进展, 2013, 32, 2156.)
|
|
[5] |
Fang, C. X.; Yu, Y.; Wang, Y. T.; Qu, Y. X. Modern Chem. Ind. 2013, 32, 16. (in Chinese)
|
(房承宣, 于泳, 王亚涛, 屈一新, 现代化工, 2013, 32, 16.)
|
|
[6] |
Hu, X.-Q.; Lichte, D.; Rodstein, I.; Weber, P.; Seitz, A.-K.; Scherpf, T.; Gessner, V. H.; Gooßen, L. J. Org. Lett. 2019, 21, 7558.
doi: 10.1021/acs.orglett.9b02830 |
[7] |
Wang, C. P.; Dong, G. B. J. Am. Chem. Soc. 2018, 140, 6057.
doi: 10.1021/jacs.8b03530 |
[8] |
Wang, J; Deng, Z. X.; Wang, C. M.; Xia, P. J.; Xiao, J. A.; Xiang, H. Y.; Chen, X. Q.; Yang, H. Org. Lett. 2018, 20, 7535.
doi: 10.1021/acs.orglett.8b03292 |
[9] |
Juliane, N. B. D.; Pelin, J.; Gerbelli, B. B.; Edwards, C. J. C.; Aguilar, A. M.; Castelletto, V.; Hamley, I. W.; Alves, W. A. Langmuir 2020, 36, 2767.
doi: 10.1021/acs.langmuir.0c00198 pmid: 32131599 |
[10] |
Garg, Y.; Tanaka, F. Org. Lett. 2020, 22, 4542.
doi: 10.1021/acs.orglett.0c01561 |
[11] |
Yin, Z. Y.; Guo, J. X.; Zhang, R.; Hu, X. Y.; Borovkov, V. J. Org. Chem. 2020, 85, 10369.
doi: 10.1021/acs.joc.0c00031 |
[12] |
Kaplaneris, N.; Koutoulogenis, G.; Raftopoulou, M.; Kokotos, C. G. J. Org. Chem. 2015, 80, 5464.
doi: 10.1021/acs.joc.5b00283 pmid: 25942500 |
[13] |
Yang, C.; Zhang, K. F.; Wu, Z. J.; Yao, H. Q.; Lin, A. J. Org. Lett. 2016, 18, 5332.
pmid: 27684319 |
[14] |
Nguyen, K. D.; Kutzscher, C.; Drache, F.; Senkovska, I.; Kaskel, S. Inorg. Chem. 2018, 57, 1483.
doi: 10.1021/acs.inorgchem.7b02854 pmid: 29364659 |
[15] |
Ipatieff, V. N.; Haensel, V. J. Org. Chem. 1942, 7, 189.
doi: 10.1021/jo01197a001 |
[16] |
Nasarow, N. D. Zh. Obshch. Khim. 1952, 22, 1147.
|
[17] |
Chen, K.; Chang, Y. P.; Gurubrahamam, R. Org. Lett. 2015, 17, 2908.
doi: 10.1021/acs.orglett.5b01040 |
[18] |
Wang, J.; Deng, Z. X.; Wang, C. M.; Xia, P. J.; Xiao, J. A.; Xiang, H. Y.; Chen, X. Q.; Yang, H. Org. Lett. 2018, 20, 7535.
doi: 10.1021/acs.orglett.8b03292 |
[19] |
Shen, L.; Xu, L.; Hou, X. H.; Liu, N.; Wu, Z. Q. Macromolecules 2018, 51, 9547.
doi: 10.1021/acs.macromol.8b02088 |
[20] |
Shen, H. C.; Zhang, L.; Chen, S. S.; Feng, J. J.; Zhang, B. W.; Zhang, Y.; Zhang, X. H.; Wu, Y. D.; Gong, L. Z. ACS Catal. 2019, 9, 791.
doi: 10.1021/acscatal.8b04654 |
[21] |
Yang, C.; Zhang, K. F.; Wu, Z. J.; Yao, H. Q.; Lin, A. J. Org. Lett. 2016, 18, 5332.
pmid: 27684319 |
[22] |
Chen, J. J.; Chang, D.; Xiao, F. H.; Deng, G.-J. Green Chem. 2018, 20, 5459.
doi: 10.1039/C8GC02654H |
[23] |
Chen, J. J.; Meng, H. X.; Zhang, F.; Xiao, F. H.; Deng, G.-J. Green Chem. 2019, 21, 5201.
doi: 10.1039/C9GC02077B |
[24] |
Cao, X. X.; Bai, Y.; Xie, Y. J.; Deng, G.-J. J. Mol. Catal. A: Chem. 2014, 383, 94.
|
[25] |
Zhang, J. W.; Jiang, Q. Q.; Yang, D. J.; Zhao, X. M.; Dong, Y. L.; Liu, R. H. Chem. Sci. 2015, 6, 4674.
doi: 10.1039/C5SC01044F |
[26] |
Shah, M.; Guo, Q. X.; Fu, Y. Catal. Commun. 2017, 89, 60.
doi: 10.1016/j.catcom.2016.10.019 |
[27] |
Taniguchi, K.; Jin, X. J.; Yamaguchi, K.; Mizuno, N. Catal. Sci. Technol. 2016, 6, 3929.
doi: 10.1039/C5CY01908G |
[28] |
Shimomoto, Y.; Matsubara, R.; Hayashi, M. Adv. Synth. Catal. 2018, 360, 3297.
doi: 10.1002/adsc.v360.17 |
[29] |
Koizumi, Y.; Jin, X. J.; Yatabe, T. F.; Miyazaki, R.; Hasegawa, J.-Y.; Nozaki, K.; Mizuno, N.; Yamaguchi, K. Angew. Chem., Int. Ed. 2019, 58, 10893.
doi: 10.1002/anie.v58.32 |
[30] |
Lin, W.-C.; Yatabe, T. F.; Yamaguchi, K. Chem. Commun. 2021, 57, 6530.
doi: 10.1039/D1CC01686E |
[31] |
Lu, C. G.; Huang, H. W.; Tuo, X. L.; Jiang, P. Y.; Zhang, F.; Deng, G.-J. Org. Chem. Front. 2019, 6, 2738.
doi: 10.1039/C9QO00603F |
[32] |
Chen, Y.; Xiao, F. H.; Chen, H.; Liu, S. W.; Deng, G.-J. RSC Adv. 2014, 4, 44621.
doi: 10.1039/C4RA08014A |
[33] |
Liang, Y.-F.; Li, X. Y.; Wang, X. Y.; Zou, M. C.; Tang, C. H.; Liang, Y. J.; Song, S.; Jiao, N. J. Am. Chem. Soc. 2016, 138, 12271.
doi: 10.1021/jacs.6b07269 |
[34] |
Xiong, M. T.; Gao, Z.; Liang, X.; Cai, P. F.; Zhu, H. P.; Pan, Y. J. Chem. Commun. 2018, 54, 9679.
doi: 10.1039/C8CC05320K |
[35] |
Wang, Z.; Chen, X. G.; Xie, H.; Wang, D. H.; Huang, H. W.; Deng, G.-J. Org. Lett. 2018, 20, 5470.
doi: 10.1021/acs.orglett.8b02387 |
[36] |
Zeng, H. Y.; Yu, J. J.; Li, C.-J. Chem. Commun. 2020, 56, 1239.
doi: 10.1039/C9CC09347H |
[37] |
Wu, Y.-H.; Wang, N.-X., Zhang, T.; Yan, Z.; Xu, B.-C.; Inoa, J.; Xing, Y. Adv. Synth. Catal. 2019, 361, 3008.
doi: 10.1002/adsc.v361.12 |
[38] |
Zhen Wang, Z.; Li, C.; Huang, H. W.; Deng, G.-J. J. Org. Chem., 2020, 85, 9415.
doi: 10.1021/acs.joc.0c01122 pmid: 32578988 |
[39] |
Chen, J. J.; Chang, D.; Xiao, F. H.; Deng, G.-J. Green Chem. 2018, 20, 5459.
doi: 10.1039/C8GC02654H |
[40] |
Nguyen, T. B.; Nguyen, L. A.; Retailleau, P. Org. Lett. 2019, 21, 6570.
doi: 10.1021/acs.orglett.9b02558 pmid: 31386376 |
[41] |
Chen, J. J.; Meng, H. X.; Zhang, F.; Xiao, F. H.; Deng, G.-J. Green Chem. 2019, 21, 5201.
doi: 10.1039/C9GC02077B |
[42] |
Lin, Y.-M.; Lu, G.-P.; Wang, R.-K.; Yi, W.-B. Org. Lett. 2016, 18, 6424.
doi: 10.1021/acs.orglett.6b03324 |
[43] |
Jiang, P. Y.; Chen, S. P.; Huang, H. W.; Hu, K.; Xia, Y.; Deng, G.-J. Green Synth. Catal. 2021, 2, 78.
|
[44] |
Li, X.; Song, Z.-R.; Chen, X.; Cai, Y.-C.; Liu, Y.-J.; Chen, C.-X.; Peng, J.-S. Chin. J. Org. Chem. 2020, 40, 950. (in Chinese)
doi: 10.6023/cjoc201909040 |
(李雪, 宋子锐, 陈鑫, 蔡轶超, 刘雅婕, 陈春霞, 彭进松, 有机化学, 2020, 40, 950.)
doi: 10.6023/cjoc201909040 |
|
[45] |
Zhang, Y.-H.; Wu, W.-J.; Zhang, K.-X.; Li, S.-S.; Hao, W.-Y. Chin. J. Org. Chem. 2021, 41, 1982. (in Chinese)
|
(张亚辉, 吴文锦, 张可心, 黎双双, 郝文燕, 有机化学, 2021, 41, 1982.)
doi: 10.6023/cjoc202012007 |
|
[46] |
Xie, Y. J.; Wu, J.; Che, X. Z.; Chen, Y.; Huang, H. W.; Deng, G.-J. Green Chem. 2016, 18, 667.
doi: 10.1039/C5GC01978H |
[47] |
Nguyen, T. B.; Ermolenko, L.; Retailleau, P.; Al-Mourabit, A. Org. Lett. 2016, 18, 2177.
doi: 10.1021/acs.orglett.6b00823 pmid: 27088653 |
[48] |
Nguyena, T. B.; Retailleau, P. Adv. Synth. Catal. 2017, 359, 3843.
doi: 10.1002/adsc.v359.21 |
[49] |
Xie, Y. J.; Chen, X. G.; Wang, Z.; Huang, H. W.; Yi, B.; Deng, G.-J. Green Chem. 2017, 19, 4294.
doi: 10.1039/C7GC02014G |
[50] |
Chen, X. G.; Wang, Z.; Huang, H. W.; Deng, G. J. Adv. Synth. Catal. 2018, 360, 4017.
doi: 10.1002/adsc.v360.20 |
[51] |
Wen, L. X.; Tang, L.; Yang, Y.; Zha, Z. G.; Wang, Z. Y. Org. Lett. 2016, 18, 1278.
doi: 10.1021/acs.orglett.6b00193 |
[52] |
Wu, J.; Xie, Y. J.; Chen, X. G.; Deng, G.-J. Adv. Synth. Catal. 2016, 358, 3206.
doi: 10.1002/adsc.201600673 |
[53] |
Wu, J.; Chen, X. G.; Xie, Y. J.; Guo, Y. J.; Zhang, Q.; Deng, G.-J. J. Org. Chem. 2017, 82, 5743.
doi: 10.1021/acs.joc.7b00556 |
[54] |
Zhang, L.-B.; Zhu, M.-H.; Ni, S.-F.; Wen, L.-R.; Li, M. ACS Catal. 2019, 9, 1680.
doi: 10.1021/acscatal.8b04933 |
[55] |
Yang, X.; Luo, G. Y.; Zhou, L. J.; Liu, B.; Zhang, X. L.; Gao, H.; Jin, Z. C.; Chi, Y. G. R. ACS Catal. 2019, 9, 10971.
doi: 10.1021/acscatal.9b03163 |
[56] |
Yu, R.-R.; Fang, X.-J. Chin. J. Org. Chem. 2021, 41, 2532. (in Chinese)
doi: 10.6023/cjoc202100048 |
(余融融, 方显杰, 有机化学, 2021, 41, 2532.)
doi: 10.6023/cjoc202100048 |
|
[57] |
Santhini, P. V.; Krishnan R, A.; Babu, S. A.; Simethy, B. S.; Das, G.; Praveen, V. K.; Sunil Varughese, S.; John, J. J. Org. Chem. 2017, 82, 10537.
doi: 10.1021/acs.joc.7b02039 pmid: 28910533 |
[58] |
Santhini, P. V.; Babu, S. A.; Krishnan R, A.; Suresh, E.; John, J. Org. Lett. 2017, 19, 2458.
doi: 10.1021/acs.orglett.7b01147 pmid: 28440656 |
[59] |
Chen, J. J.; Chang, D.; Xiao, F. H.; Deng, G.-J. J. Org. Chem. 2019, 84, 568.
doi: 10.1021/acs.joc.8b02410 |
[60] |
Li, C.; Xie, Y. J.; Xiao, F. H.; Huang, H. W.; Deng, G.-J. Chem. Commun. 2019, 55, 4079.
doi: 10.1039/C9CC00943D |
[61] |
Maeda, K.; Matsubara, R.; Hayashi, M. Org. Lett. 2021, 23, 1530.
doi: 10.1021/acs.orglett.0c04056 |
[62] |
Hong Sik Han, H. S.; Oh, E. H.; Jung, Y.-S.; Han, S. B. Org. Lett. 2018, 20, 1698.
doi: 10.1021/acs.orglett.8b00648 pmid: 29569444 |
[63] |
Shah, T. K.; Medina, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, 138, 4948.
doi: 10.1021/jacs.6b01986 |
[64] |
Iwasaki, M.; Kazao, Y.; Ishida, T.; Nishihara, Y. Org. Lett. 2020, 22, 7343.
doi: 10.1021/acs.orglett.0c02671 |
[65] |
Xing, H.-C.; Xie, P.-Z. Chin. J. Org. Chem. 2021, 41, 431. (in Chinese)
doi: 10.6023/cjoc2021006 |
(邢慧聪, 解沛忠, 有机化学, 2021, 41, 431.)
doi: 10.6023/cjoc2021006 |
|
[66] |
Liao, Y. F.; Peng, Y.; Qi, H. R.; Deng, G.-J.; Gong, H.; Li, C.-J. Chem. Commun. 2015, 51, 1031.
doi: 10.1039/C4CC08370A |
[67] |
Chen, J. J.; Li, G. Z.; Xie, Y. J.; Liao, Y. F.; Xiao, F. H.; Deng, G.-J. Org. Lett. 2015, 17, 5870.
doi: 10.1021/acs.orglett.5b03058 |
[68] |
Chen, Q. H.; Xie, R.; Jia, H. H.; Sun, J. L.; Lu, G. P.; Jiang, H. F.; Zhang, M. J. Org. Chem. 2020, 85, 5629.
doi: 10.1021/acs.joc.0c00562 |
[69] |
Jiang, P. Y.; Chen, S. P.; Xia, Y.; Zhang, Q. Q.; Deng, G.-J. Org. Lett. 2020, 22, 8076.
doi: 10.1021/acs.orglett.0c03023 |
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