Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation

doi:10.6023/cjoc201808017

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 59-73.DOI: 10.6023/cjoc201808017 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞；碳氢活化合辑2018-2019

Reviews

过渡金属催化的区域选择性芳烃C—H键氧化生成C—O键

杨帆致^a, 张晗^b, 刘旭日^b, 王博^b, Lutz Ackermann^c

a 北京理工大学前沿交叉科学研究院北京 100081;
b 北京理工大学化学与化工学院北京 100081;
c 哥廷根大学有机与生物分子化学研究所哥廷根德国 37077

收稿日期:2018-08-16 修回日期:2018-10-22 发布日期:2018-10-26
通讯作者: 杨帆致, 王博, Lutz Ackermann E-mail:yangfanzhi@bit.edu.cn;bowang@bit.edu.cn;Lutz.Ackermann@chemie.uni-goettingen.de
基金资助:
国家自然科学基金（No.21801018）和北京理工大学青年教师学术启动计划（No.1230011181807）资助项目.

Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation

Yang Fanzhi^a, Zhang Han^b, Liu Xuri^b, Wang Bo^b, Ackermann Lutz^c

a Advanced Research Institute of Multidisciplinary Science, Beijing Institute of Technology, Beijing 100081, China;
b School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081 China;
c Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Göttingen 37077 Germany

Received:2018-08-16 Revised:2018-10-22 Published:2018-10-26
Contact: 10.6023/cjoc201808017 E-mail:yangfanzhi@bit.edu.cn;bowang@bit.edu.cn;Lutz.Ackermann@chemie.uni-goettingen.de
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21801018) and the Beijing Institute of Technology Research Fund Program for Young Scholars (No. 1230011181807).

Recent years the great progress in transition metal-catalyzed direct aromatic C—H oxidation has been witnessed, which has been utilized in the preparation of various phenolic compounds. These transformations employ inter alia palladium, copper, ruthenium, iridium, etc. as the transition metal catalysts, and hypervalent iodine, persulfate, or oxygen as the oxidants. There have been several reviews in which the C—H oxidations with specific transition metal or oxidant was discussed. This review focuses specifically on transition metal-catalyzed aromatic C—H oxidations with ortho-, meta-, or para-selectivity, and rationalizes the possible generation mechanism of regio-selectivities, which might be controlled by the directing group via chelation-assistance, the ligand, or intrinsic properties of the substrate. The discussion section indicated the existing problems of transition metal-catalyzed aromatic C—H oxidations, as well as the possible limiting factors for the development and application of this strategy.

Key words: transition metal, arene, C—H oxidation, regio-selectivity, directing group

Cite this article

Yang Fanzhi, Zhang Han, Liu Xuri, Wang Bo, Ackermann Lutz. Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation[J]. Chin. J. Org. Chem., 2019, 39(1): 59-73.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim, 2003.
(b) Fiegel, H.; Voges, H. W.; Hamamoto, T.; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H. J.; Garbe, D.; Paulus, W. Phenol Derivatives in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, New York, 2002.
(c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, Ed.:Negishi, E.-I., Wiley-Interscience, New York, 2002, p. 1097.
(d) Tyman, J. H. P. Synthetic and Natural Phenols, Elsevier, New York, 1996.
(e) Liao, S.; Zhang, G.; Cao, H.; Chen, B.; Li, W.; Wu, X.; Feng, Y. Chin. J. Org. Chem. 2018, 38, 1549.
(f) Lin, W.; Cai, Q.; Zheng, C.; Huang, Z.; Shi, D. Chin. J. Org. Chem. 2017, 37, 2094.
(g) Li, Z.; Kang, S.; Chen, L.; Wang, Y.; Li, J. Chin. J. Org. Chem. 2016, 36, 1143.
[2] Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[3] Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.
[4] Thirunavukkarasu, V. S.; Kozhushkov, S. I.; Ackermann, L. Chem. Commun. 2014, 50, 29.
[5] Newhouse, T.; Baran, P. S. Angew. Chem. Int. Ed. 2011, 50, 3362.
[6] Liang, Y.-F.; Jiao, N. Acc. Chem. Res. 2017, 50, 1640.
[7] Mandal, S.; Bera, T.; Dubey, G.; Saha, J.; Laha, J. K. ACS Catal. 2018, 8, 5085.
[8] (a) Huang, Z.; Dong, G. Acc. Chem. Res. 2017, 50, 465.
(b) Hartwig, J. F. Acc. Chem. Res. 2017, 50, 549.
(c) Kozlowski, M. C. Acc. Chem. Res. 2017, 50, 638.
[9] For selected recent examples, see:(a) Raghuvanshi, K.; Zell, D.; Ackermann, L. Org. Lett. 2017, 19, 1278.
(b) Raghuvanshi, K.; Rauch, K.; Ackermann, L. Chem.-Eur. J. 2015, 21, 1790.
(c) Hao, X.-Q.; Chen, L.-J.; Ren, B.; Li, L.-Y.; Yang, X.-Y.; Gong, J.-F.; Niu, J.-L.; Song M.-P. Org. Lett. 2014, 16, 1104.
(d) Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105.
(e) Zhang, C.; Sun, P. J. Org. Chem. 2014, 79, 8457.
(f) Péron, F.; Fossey, C.; Sopkova-de Oliveira Santos, J.; Cailly, T.; Fabis, F. Chem.-Eur. J. 2014, 20, 7507.
(g) Bhadra, S.; Dzik, W. I.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 2959.
(h) Bhadra, S.; Matheis, C.; Katayev, D.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 9279.
(i) Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
(j) Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842.
(k) Eom, D.; Jeong, Y.; Kim, Y. R.; Lee, E.; Choi, W.; Lee, P. H. Org. Lett. 2013, 15, 5210.
(l) Zhao, J.; Wang, Y.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2012, 14, 1078.
(m) Zhao, J.; Zhang, Q.; Liu, L.; He, Y.; Li, J.; Li, J.; Zhu, Q. Org. Lett. 2012, 14, 5362.
(n) Li, W.; Sun, P. J. Org. Chem. 2012, 77, 8362.
(o) Jiang, T.-S.; Wang, G.-W. J. Org. Chem. 2012, 77, 9504.
(p) Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu L. J. Am. Chem. Soc. 2011, 133, 9250.
(q) Anand, M.; Sunoj, R. B. Org. Lett. 2011, 13, 4802.
(r) Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504.
(s) Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203.
(t) Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476.
[10] For selected reviews and recent examples, see:(a) Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27.
(b) Tang, S.; Zeng, L.; Lei, A. J. Am. Chem. Soc. 2018, 140, 13128.
(c) Ma, C.; Fang, P.; Mei, T.-S. ACS Catal. 2018, 8, 7179.
(d) Sauermann, N.; Meyer, T. H.; Qiu, Y.; Ackermann, L. ACS Catal. 2018, 8, 7086.
(e) Sauermann, N.; Meyer, T. H.; Ackermann, L. Chem.-Eur. J. 2018, 24, 16209.
(f) Jiao, K.-J.; Li, Z.-M.; Xu, X.-T.; Zhang, L.-P.; Li, Y.-Q.; Zhang, K.; Mei, T.-S. Org. Chem. Front. 2018, 5, 2244.
(g) Shao, A.; Li, N.; Gao, Y.; Zhan, J.; Chiang, C.-W.; Lei, A. Chin. J. Chem. 2018, 36, 619.
(h) Yang, Q.-L.; Fang, P.; Mei, T.-S. Chin. J. Chem. 2018, 36, 338.
(i) Jiao, K.-J.; Zhao, C.-Q.; Fang, P.; Mei, T.-S. Tetrahedron Lett. 2017, 58, 797.
(j) Yuan, Y.; Chen, Y.; Tang, S.; Huang, Z.; Lei, A. Sci. Adv. 2018, 4, eaat5312.
(k) Shrestha, A.; Lee, M.; Dunn, A. L.; Sanford, M. S. Org. Lett. 2018, 20, 204.
(l) Sauermann, N.; Meyer, T. H.; Tian, C.; Ackermann, L. J. Am. Chem. Soc. 2017, 139, 18452.
(m) Yang, Q.-L.; Li, Y.-Q.; Ma, C.; Fang, P.; Zhang, X.-J.; Mei, T.-S. J. Am. Chem. Soc. 2017, 139, 3293.
(n) Li, Y.-Q.; Yang, Q.-L.; Fang, P.; Mei, T.-S.; Zhang, D. Org. Lett. 2017, 19, 2905.
[11] A recent example:Zhang, Z.-J.; Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2014, 16, 3292.
[12] (a) Jintoku, T.; Taniguchi, H.; Fujiwara, Y. Chem. Lett. 1987, 1865.
(b) Jintoku, T.; Takaki, K.; Fujiwara, Y.; Fuchita Y.; Hiraki, K. Bull. Chem. Soc. Jpn. 1990, 63, 438.
(c) Jintoku, T.; Nishimura, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1990, 1687.
[13] Yamada, S.; Sakaguchi, S.; Ishii, Y. J. Mol. Catal. A Chem. 2007, 262, 48.
[14] Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A: Chem. 1996, 108, 35.
[15] Cook, A. K.; Sanford, M. S. J. Am. Chem. Soc. 2015, 137, 3109.
[16] Gary, J. B.; Cook, A. K.; Sanford, M. S. ACS Catal. 2013, 3, 700.
[17] Shibahara, F.; Kinoshita, S.; Nozaki, K. Org. Lett. 2004, 6, 2437.
[18] Chen, C.-D.; Sheng, W.-B.; Shi, G.-J.; Guo, C.-C. J. Phys. Org. Chem. 2013, 26, 23.
[19] Casella, L.; Rigoni, L. J. Chem. Soc., Chem. Commun. 1985, 1668.
[20] Réglier, M.; Amadeï, E.; Tadayoni, R.; Waegell, B. J. Chem. Soc., Chem. Commun. 1989, 447.
[21] Cruse, R. W.; Kaderli, S.; Meyer, C. J.; Zuberbühler, A. D.; Karlin, K. D. J. Am. Chem. Soc. 1988, 110, 5020.
[22] Reinaud, O.; Capdevielle, P.; Maumy, M. J. Chem. Soc., Chem. Commun. 1990, 566.
[23] Takizawa, Y.; Tateishi, A.; Sugiyama, J.; Yoshida, H.; Yoshihara, N. J. Chem. Soc., Chem. Commun. 1991, 104.
[24] Singh, B. K.; Jana, R. J. Org. Chem. 2016, 81, 831.
[25] Chen, X.; Hao, X.-S.; Goodhue, C.-E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
[26] (a) Valk, J.-M.; van Belzen, R.; Boersma, J.; Spek, A. L.; van Koten, G. J. Chem. Soc., Dalton Trans. 1994, 2293.
(b) Valk, J.-M.; Boersma, J.; van Koten, G. Organometallics 1996, 15, 4366.
[27] Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654.
[28] Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew. Chem., Int. Ed. 2012, 51, 13070.
[29] Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
[30] Subba Reddy, B. V.; Umadevi, N.; Narasimhulu, G.; Yadav, J. S. Tetrahedron Lett. 2012, 53, 6091.
[31] Zhao, Q.; Poisson, T.; Pannecoucke, X.; Besset, T. Synthesis 2017, 49, 4808.
[32] Gandeepan, P.; Ackermann, L. Chem 2018, 4, 199.
[33] Chen, X.-Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 6280.
[34] Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
[35] Liang, Y.-F.; Wang, X.; Yuan, Y.; Liang, Y.; Li, X.; Jiao, N. ACS Catal. 2015, 5, 6148.
[36] Nguyen, T. H. L.; Gigant, N.; Delarue-Cochin, S.; Joseph, D. J. Org. Chem. 2016, 81, 1850.
[37] Qian, C.; Lin, D.; Deng, Y.; Zhang, X.-Q.; Jiang, H.; Miao, G.; Tang, X.; Zeng, W. Org. Biomol. Chem. 2014, 12, 5866.
[38] Zhang, D.; Cui, X.; Yang, F.; Zhang, Q.; Zhu, Y.; Wu, Y. Org. Chem. Front. 2015, 2, 951.
[39] Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.
[40] Irastorza, A.; Aizpurua, J. M.; Correa, A. Org. Lett. 2016, 18, 1080.
[41] Kim, S. H.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 5863.
[42] Dong, J.; Liu, P.; Sun, P. J. Org. Chem. 2015, 80, 2925.
[43] Yamaguchi, T.; Yamaguchi, E.; Tada, N.; Itoh, A. Adv. Synth. Catal. 2015, 357, 2017.
[44] Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.
[45] Stowers, K. J.; Sanford, M. S. Org. Lett. 2009, 11, 4584.
[46] Powers, D. C.; Geibel, M. A. L.; Klein, J. E. M. N.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050.
[47] Powers, D. C.; Xiao, D. Y.; Geibel, M. A. L.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 14530.
[48] Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.-F.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827.
[49] Desai, L. V; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285.
[50] Wang, G.-W.; Yuan, T.-T.; Wu, X.-L. J. Org. Chem. 2008, 73, 4717.
[51] Sun, Y.-H.; Sun, T.-Y.; Wu, Y.-D.; Zhang, X.; Rao, Y. Chem. Sci. 2016, 7, 2229.
[52] Yang, X.; Sun, Y.; Chen, Z.; Rao, Y. Adv. Synth. Catal. 2014, 356, 1625.
[53] A review:Parasram, M.; Gevorgyan, V. Acc. Chem. Res. 2017, 50, 2038.
[54] (a) Chernyak, N.; Dudnik, A. S.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 8270.
(b) Huang, C.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Adv. Synth. Catal. 2011, 353, 1285.
(c) Gulevich, A. V.; Melkonyan, F. S.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 5528.
[55] (a) Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 17630.
(b) Huang, C.; Ghavtadze, N.; Godoi, B.; Gevorgyan, V. Chem.-Eur. J. 2012, 18, 9789.
[56] Yang, Y.; Lin, Y.; Rao, Y. Org. Lett. 2012, 14, 2874.
[57] Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032.
[58] Thirunavukkarasu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett. 2012, 14, 4210.
[59] Yang, F.; Ackermann, L. Org. Lett. 2013, 15, 718.
[60] Thirunavukkarasu, V. S.; Ackermann, L. Org. Lett. 2012, 14, 6206.
[61] Shan, G.; Han, X.; Lin, Y.; Yu, S.; Rao, Y. Org. Biomol. Chem. 2013, 11, 2318.
[62] Kim, K.; Choe, H.; Jeong, Y.; Lee, J. H.; Hong, S. Org. Lett. 2015, 17, 2550.
[63] Yang, F.; Rauch, K.; Kettelhoit, K.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 11285.
[64] Shome, S.; Singh, S. P. Tetrahedron Lett. 2017, 58, 3743.
[65] Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728.
[66] Yang, X.; Shan, G.; Rao, Y. Org. Lett. 2013, 15, 2334.
[67] Liu, W.; Ackermann, L. Org. Lett. 2013, 15, 3484.
[68] Turlington, C. R.; Morris, J.; White, P. S.; Brennessel, W. W.; Jones, W. D.; Brookhart, M.; Templeton, J. L. Organometallics 2014, 33, 4442.
[69] Wu, Q.; Yan, D.; Chen, Y.; Wang, T.; Xiong, F.; Wei, W.; Lu, Y.; Sun, W.-Y.; Li, J. J.; Zhao, J. Nat. Commun. 2017, 8, 14227.
[70] Cook, A. K.; Emmert, M. H.; Sanford, M. S. Org. Lett. 2013, 15, 5428.
[71] For selected recent views on template-directed meta-selective C(sp²)-H functionalizations, see:(a) Mihai, M. T.; Genov, G. R.; Phipps, R. J. Chem. Soc. Rev. 2017, 47, 149.
(b) Ping, L.; Chung, D. S.; Bouffard, J.; Lee, S.-G. Chem. Soc. Rev. 2017, 46, 4299.
(c) Mihai, M. T.; Phipps, R. J. Synlett 2017, 28, 1011.
(d) Dey, A.; Agasti, S.; Maiti, D. Org. Biomol. Chem. 2016, 14, 5440.
(e) Yang, G.; Butt, N.; Zhang, W. Chin. J. Catal. 2016, 37, 98.
(f) Yang, G.; Butt, N.; Zhang, W. Chin. J. Catal. 2016, 37, 98.
(g) Ackermann, L.; Li, J. Nat. Chem. 2015, 7, 686.
(h) Yang, J. Org. Biomol. Chem. 2015, 13, 1930.
[72] (a) Bera, M.; Sahoo, S. K.; Maiti, D. ACS Catal. 2016, 6, 3575.
(b) Maji, A.; Bhaskararao, B.; Singha, S.; Sunoj, R. B.; Maiti, D. Chem. Sci. 2016, 7, 3147.
[73] Bag, S.; Patra, T.; Modak, A.; Deb, A.; Maity, S.; Dutta, U.; Dey, A.; Kancherla, R.; Maji, A.; Hazra, A.; Bera, M.; Maiti, D. J. Am. Chem. Soc. 2015, 137, 11888.
[74] A review on template-directed para-selective C(sp²)-H functionalizations:Dey, A.; Maity, S.; Maiti, D. Chem. Commun. 2016, 52, 12398.

过渡金属催化的区域选择性芳烃C—H键氧化生成C—O键

Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447.
[2]	Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.
[3]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[4]	Xiaoyang Gao, Ruirui Zhai, Xun Chen, Shuojin Wang. Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3119-3134.
[5]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[6]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[7]	Sifan Dong, Haolong Li, Yuan Qin, Shiming Fan, Shouxin Liu. Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2351-2367.
[8]	Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446.
[9]	Guangli Xu, Jing Xu, Haidong Xu, Xiang Cui, Xingzhong Shu. Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1899-1933.
[10]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.
[11]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[12]	Ling Liu, Taotao Hao, Wanhua Wu, Cheng Yang. Stilbene-Based Molecular Switches with Aggregation Induced Emission (AIE) Function Constructed by Supramolecular Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2189-2196.
[13]	Jiao Qin, Jie Chen, Yan Su. Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2171-2177.
[14]	Wang Jiang, Zhuangzhi Shi. Recent Progress in meta-/para-Selective Aromatic C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1691-1705.
[15]	Yi Zhang, Cheng-Zhuo Du, Ji-Kun Li, Xiao-Ye Wang. Recent Advances in Multi-Resonance Thermally Activated Delayed Fluorescence Materials Based on B,N-Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1645-1690.