过渡金属催化的区域选择性芳烃C—H键氧化生成C—O键

doi:10.6023/cjoc201808017

有机化学 ›› 2019, Vol. 39 ›› Issue (1): 59-73.DOI: 10.6023/cjoc201808017 上一篇下一篇

所属专题：庆祝陈庆云院士九十华诞；碳氢活化合辑2018-2019

综述与进展

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).

文章分享

摘要/Abstract

近年来过渡金属催化的芳烃直接C—H氧化反应取得了重要进展，该策略被用于多种酚类化合物的制备.反应体系使用的过渡金属催化剂包括钯、铜、钌、铱等；氧化剂包括高价碘化合物、过硫酸盐、氧气等.此前已有多篇综述就特定的过渡金属或氧化剂参与的C—H氧化反应进行了详尽的讨论.本综述着重探讨过渡金属催化的邻、间、对位选择性的芳烃C—H氧化反应，并试图阐释上述区域选择性的产生机制，其中包括导向基团的螯合辅助作用、配体控制、底物自身因素等.在讨论部分提出了过渡金属催化的芳烃C—H氧化反应中存在的问题以及影响该策略发展应用的可能限制因素.

关键词: 过渡金属, 芳烃, C-H氧化, 区域选择性, 导向基团

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

引用此文

杨帆致, 张晗, 刘旭日, 王博, Lutz Ackermann. 过渡金属催化的区域选择性芳烃C—H键氧化生成C—O键[J]. 有机化学, 2019, 39(1): 59-73.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[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

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	付雅彤, 孙超凡, 张丹, 金成国, 陆居有. 巢式-碳硼烷硼氢键官能化反应研究进展[J]. 有机化学, 2024, 44(2): 438-447.
[2]	张剑, 梁万洁, 杨艺, 闫法超, 刘会. 联烯胺化合物的区域选择性双官能团化[J]. 有机化学, 2024, 44(2): 335-348.
[3]	刘杰, 韩峰, 李双艳, 陈天煜, 陈建辉, 徐清. 无过渡金属参与甲基杂环化合物与醇的选择性有氧烯基化反应[J]. 有机化学, 2024, 44(2): 573-583.
[4]	董江湖, 宣良明, 王池, 赵晨熙, 王海峰, 严琼姣, 汪伟, 陈芬儿. 无过渡金属或无光催化剂条件下可见光促进喹喔啉酮C(3)—H官能团化研究进展[J]. 有机化学, 2024, 44(1): 111-136.
[5]	赵红琼, 于淼, 宋冬雪, 贾琦, 刘颖杰, 季宇彬, 许颖. 羧酸脱羧羟基化反应研究进展[J]. 有机化学, 2024, 44(1): 70-84.
[6]	王文芳. 过渡金属催化不对称C—H硼化反应研究进展[J]. 有机化学, 2023, 43(9): 3146-3166.
[7]	高晓阳, 翟锐锐, 陈训, 王烁今. 碳酸亚乙烯酯参与C—H键活化反应的研究进展[J]. 有机化学, 2023, 43(9): 3119-3134.
[8]	刘露, 张曙光, 胡仁威, 赵晓晓, 崔京南, 贡卫涛. 基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO₂催化转化[J]. 有机化学, 2023, 43(8): 2808-2814.
[9]	陈新强, 张敬. 伯醇的脱羟甲基反应的研究进展[J]. 有机化学, 2023, 43(8): 2711-2719.
[10]	范威. O₂促进下五元环烯胺的C—H亚胺化[J]. 有机化学, 2023, 43(7): 2492-2498.
[11]	石义军, 孙馨悦, 曹晗, 别福升, 马杰, 刘哲, 丛兴顺. 室温下酯与伯硫醇的硫酯化反应[J]. 有机化学, 2023, 43(7): 2499-2505.
[12]	董思凡, 李昊龙, 秦源, 范士明, 刘守信. 氨基酸作为瞬态导向基在碳氢键活化反应中的研究进展[J]. 有机化学, 2023, 43(7): 2351-2367.
[13]	徐忠荣, 万结平, 刘云云. 基于热、光以及电化学过程的无过渡金属碳-氢键硫氰化和硒氰化反应[J]. 有机化学, 2023, 43(7): 2425-2446.
[14]	褚杨杨, 韩召斌, 丁奎岭. 动力学拆分在过渡金属催化的不对称(转移)氢化中的应用研究[J]. 有机化学, 2023, 43(6): 1934-1951.
[15]	户晓兢, 郭斐翔, 朱润青, 周柄棋, 张涛, 房立真. 对烷氧基酚的合成及其去芳构化后的合成应用[J]. 有机化学, 2023, 43(6): 2239-2244.