Recent Progress in C(sp3)-H Asymmetric Oxidation Catalyzed by Bioinspired Metal Complexes
- Corresponding author: Sun Wei, wsun@licp.cas.cn
Citation:
Sun Qiangsheng, Sun Wei. Recent Progress in C(sp3)-H Asymmetric Oxidation Catalyzed by Bioinspired Metal Complexes[J]. Chinese Journal of Organic Chemistry,
;2020, 40(11): 3686-3696.
doi:
10.6023/cjoc202006008
(a) Guo, M.; Corona, T.; Ray, K.; Nam, W. ACS Cent. Sci. 2019, 5, 13.
(b) Ray, K.; Pfaff, F. F.; Wang, B.; Nam, W. J. Am. Chem. Soc. 2014, 136, 13942.
(c) Yin, G. Acc. Chem. Res. 2013, 46, 483.
(d) Que, L. Jr.; Tolman, W. B. Nature 2008, 455, 333.
Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds, CRC press, Boca Raton, 2003.
Asensio, G.; Castellano, G.; Mello, R.; González Núñez, M. E. J. Org. Chem. 1996, 61, 5564.
doi: 10.1021/jo9604189
Chen, M. S.; White, M. C. Science 2007, 318, 783.
doi: 10.1126/science.1148597
Asensio, G.; González Núñez, M. E.; Bernardini, C. B.; Mello, R.; Adam, W. J. Am. Chem. Soc. 1993, 115, 7250.
doi: 10.1021/ja00069a025
Lee, M.; Sanford, M. S. J. Am. Chem. Soc. 2015, 137, 12796.
doi: 10.1021/jacs.5b09099
Tenaglia, A.; Terrenova, E.; Waegell, B. J. Org. Chem. 1992, 57, 5523.
doi: 10.1021/jo00046a040
Gómez, L.; Garcia-Bosch, I.; Company, A.; Benet-Buchholz, J.; Polo, A.; Sala, X.; Ribas, X.; Costas, M. Angew. Chem., Int. Ed. 2009, 48, 5720.
doi: 10.1002/anie.200901865
Chen, K.; Eschenmoser, A.; Baran, P. S. Angew. Chem., Int. Ed. 2009, 48, 9705.
doi: 10.1002/anie.200904474
Du, X.; Houk, K. N. J. Org. Chem. 1998, 63, 6480.
doi: 10.1021/jo9801519
(a) Ortiz de Montellano, P. R. Chem. Rev. 2010, 110, 932.
(b) Abu-Omar, M. M.; Loaiza, A.; Hontzeas, N. Chem. Rev. 2005, 105, 2227.
(a) Groves, J. T.; Viski, P. J. Am. Chem. Soc. 1989, 111, 8537.
(b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628.
Gross, Z.; Ini, S. Org. Lett. 1999, 1, 2077.
doi: 10.1021/ol991131b
Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 2441.
Srour, H.; Le Maux, P.; Simonneaux, G. Inorg. Chem. 2012, 51, 5850.
doi: 10.1021/ic300457z
Maux, P. L.; Srour, H. F.; Simonneaux, G. Tetrahedron 2012, 68, 5824.
doi: 10.1016/j.tet.2012.05.014
Frost, J. R.; Huber, S. M.; Breitenlechner, S.; Bannwarth, C.; Bach, T. Angew. Chem., Int. Ed. 2015, 54, 691.
(a) Fackler, P.; Berthold, C.; Voss, F.; Bach, T. J. Am. Chem. Soc. 2010, 132, 15911.
(b) Fackler, P.; Huber, S. M.; Bach, T. J. Am. Chem. Soc. 2012, 134, 12869.
Burg, F.; Gicquel, M.; Breitenlechner, S.; Pöthig, A.; Bach, T. Angew. Chem., Int. Ed. 2018, 57, 2953.
doi: 10.1002/anie.201712340
Burg, F.; Breitenlechner, S.; Jandl, C.; Bach, T. Chem. Sci. 2020, 11, 2121.
doi: 10.1039/C9SC06089H
(a) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189.
(b) Bhatia, B.; Punniyamurthy, T.; Iqbal, J. In Asymmetric Oxidation Reactions, Ed.: Katsuki, T., Oxford University Press, New York, 2001, p. 1~15.
(c) Matsumoto, K.; Saito, B.; Katsuki, T. Chem. Commun. 2007, 3619.
(d)Fan, Q.-H.; Ding, K. Top. Organomet. Chem. 2011, 36, 207.
(e) Shaw, S.; White, J. D. Chem. Rev. 2019, 119, 9381.
Hamachi, K.; Irie, I.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979.
doi: 10.1016/0040-4039(96)00984-7
Miyafuji, A.; Katsuki, T. Tetrahedron 1998, 54, 10339.
doi: 10.1016/S0040-4020(98)00489-X
Punniyamurthy, T.; Miyafuji, A.; Katsuki, T. Tetrahedron Lett. 1998, 39, 8295.
doi: 10.1016/S0040-4039(98)80001-4
Murahashi, S. I.; Noji, S.; Komiya, N. Adv. Synth. Catal. 2004, 346, 195.
doi: 10.1002/adsc.200303190
Murahashi, S.; Noji, S.; Hirabayashi, T.; Komiya, N. Tetrahedron: Asymmetry 2005, 16, 3527.
doi: 10.1016/j.tetasy.2005.08.056
Milan, M.; Bietti, M.; Costas, M. ACS Cent. Sci. 2017, 3, 196.
doi: 10.1021/acscentsci.6b00368
(a) Mas-Ballesté, R.; Que, L. Jr. J. Am. Chem. Soc. 2007, 129, 15964.
(b) Lyakin, O. Y.; Ottenbacher, R. V.; Bryliakov, K. P.; Talsi, E. P. ACS Catal. 2012, 2, 1196.
(a) Du, J.; Miao, C.; Xia, C.; Lee, Y.-M.; Nam, W.; Sun, W. ACS Catal. 2018, 8, 4528.
(b) Li, X.-X.; Guo, M.; Qiu, B.; Cho, K.-B.; Sun, W.; Nam, W. Inorg. Chem. 2019, 58, 14842.
Milan, M.; Bietti, M.; Costas, M. Org. Lett. 2018, 20, 2720.
doi: 10.1021/acs.orglett.8b00929
Talsi, E. P.; Samsonenko, D. G.; Ottenbacher, R. V.; Bryliakov, K. P. ChemCatChem 2017, 9, 4580.
doi: 10.1002/cctc.201701169
Sun, W.; Sun, Q. Acc. Chem. Res. 2019, 52, 2370.
doi: 10.1021/acs.accounts.9b00285
(a) Wang, B.; Miao, C.; Wang, S.; Xia, C.; Sun, W. Chem.-Eur. J. 2012, 18, 6750.
(b) Wang, B.; Wang, S.; Xia, C.; Sun, W. Chem.-Eur. J. 2012, 18, 7332.
(c) Wu, M.; Wang, B.; Wang, S.; Xia, C.; Sun, W. Org. Lett. 2009, 11, 3622.
(d) Miao, C.; Wang, B.; Wang, Y.; Xia, C.; Lee, Y.-M.; Nam, W.; Sun, W. J. Am. Chem. Soc. 2016, 138, 936.
(e) Shen, D.; Qiu, B.; Xu, D.; Miao, C.; Xia, C.; Sun, W. Org. Lett. 2016, 18, 372.
(f) Wang, W.; Sun, Q.; Xia, C.; Sun, W. Chin. J. Catal. 2018, 39, 1463.
Qiu, B.; Xu, D.; Sun, Q.; Miao, C.; Lee, Y.-M.; Li, X.-X.; Nam, W.; Sun, W. ACS Catal. 2018, 8, 2479.
doi: 10.1021/acscatal.7b03601
Qiu, B.; Xu, D.; Sun, Q.; Lin, J.; Sun, W. Org. Lett. 2019, 21, 618.
doi: 10.1021/acs.orglett.8b03652
Cianfanelli, M.; Olivo, G.; Milan, M.; Klein Gebbink, R. J. M.; Ribas, X.; Bietti, M.; Costas, M. J. Am. Chem. Soc. 2020, 142, 1584.
doi: 10.1021/jacs.9b12239
Hong Wu , Yuxi Wang , Hongyan Feng , Xiaokui Wang , Bangkun Jin , Xuan Lei , Qianghua Wu , Hongchun Li . Application of Computational Chemistry in the Determination of Magnetic Susceptibility of Metal Complexes. University Chemistry, 2025, 40(3): 116-123. doi: 10.12461/PKU.DXHX202405141
Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
Xueyu Lin , Ruiqi Wang , Wujie Dong , Fuqiang Huang . 高性能双金属氧化物负极的理性设计及储锂特性. Acta Physico-Chimica Sinica, 2025, 41(3): 2311005-. doi: 10.3866/PKU.WHXB202311005
Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
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
Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo2O4/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
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
Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi2O3 pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
Wenjing ZHANG , Xiaoqing WANG , Zhipeng LIU . Recent developments of inorganic metal complex-based photothermal materials and their applications in photothermal therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2356-2372. doi: 10.11862/CJIC.20240254
Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO2-0.39IrOx composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278