SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 10: 3033 - 3050

DOI: https://doi.org/10.6023/cjoc202209016

综述与进展

手性胺/金(I)协同催化的不对称串联反应研究

  • 崔效源 ,
  • 周锋 ,
  • 吴海虹 ,
  • 周剑
展开
  • a 华东师范大学化学与分子工程学院 绿色化学与化工过程绿色化上海市重点实验室 上海 200062
    b 中国科学院上海有机化学研究所 金属有机国家重点实验室 上海 200032

收稿日期: 2022-09-13

  修回日期: 2022-10-16

  网络出版日期: 2022-10-20

基金资助

国家自然科学基金(21871090); 国家自然科学基金(21971067); 上海市科技创新行动计划(20JC1416900)

收起

Asymmetric Tandem Reactions Achieved by Chiral Amine & Gold(I) Cooperative Catalysis

  • Xiaoyuan Cui ,
  • Feng Zhou ,
  • Haihong Wu ,
  • Jian Zhou
Expand
  • a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
* Corresponding authors. E-mail: ;
E-mail: ;
E-mail:

Received date: 2022-09-13

  Revised date: 2022-10-16

  Online published: 2022-10-20

Supported by

National Natural Science Foundation of China(21871090); National Natural Science Foundation of China(21971067); Shanghai Science and Technology Innovation Action Plan(20JC1416900)

Fold

摘要

协同催化是改善反应效率和选择性控制的一种有力策略. 通过组合不同催化剂来获得协同效应, 实现单一催化剂难以企及的高反应活性和选择性以及发展挑战性新反应, 是不对称催化的重要研究内容. 手性胺根据胺结构的不同, 可通过烯胺、亚胺或攫氢活化等方式来活化具有α-氢的醛(酮)、共轭烯醛(酮)、活泼次甲基或亚甲基化合物; 而阳离子型的一价金催化可以高效活化烯烃、炔烃和重氮化合物, 因此, 结合两种催化剂的特点来发展不对称串联反应, 实现从简单原料出发构建较复杂手性化合物受到关注. 本综述旨在介绍手性伯胺、仲胺或叔胺与一价金协同催化来实现的不对称串联反应, 重点关注两者协同催化的优势、避免催化剂失活的方法以及讨论未来的发展空间, 进而为从事不对称催化相关的研究人员提供一些有益参考和借鉴.

关键词： 不对称催化; 协同催化; 手性胺催化; 金催化

本文引用格式

崔效源 , 周锋 , 吴海虹 , 周剑 . 手性胺/金(I)协同催化的不对称串联反应研究[J]. 有机化学, 2022 , 42(10) : 3033 -3050 . DOI: 10.6023/cjoc202209016

Abstract

Cooperative catalysis is a powerful strategy to improve the efficiency and selectivity of organic reactions. It is of current interest in asymmetric catalysis to combine different catalysts to secure synergistic effects to realize high reaction activity and selectivity unattainable by a single catalyst, and to develop challenging new reactions. Depending on their structures, chiral amines can activate aldehydes or ketones with α-protons, conjugated enals or enones, activated methine or methylene compounds via enamine catalysis, iminium catalysis or deprotonative activation. On the other hand, cationic gold(I) catalysis can efficiently activate olefins, alkynes or diazo compounds for functionalization reactions. Therefore, it has attracted ever-increasing attention to combine the reactivity patterns of the two types of catalysts to develop asymmetric tandem reactions, and paves a facile way to construct complex chiral compounds from simple starting materials. The purpose of this review is to introduce the asymmetric tandem reactions achieved by chiral amine & gold(I) catalysis, focusing on the advantages of such type of cooperative catalysis, the way to avoid catalyst deactivation, as well as its future development, so as to provide some useful references for researchers engaged in asymmetric catalysis.

Key words： asymmetric catalysis; cooperative catalysis; chiral amine catalysis; gold catalysis

参考文献

[1]
(a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, C. G. Chem. Rev. 2005, 105, 1001.
[1]
(b) Denard, C. A.; Hartwig, J. F.; Zhao, H. ACS Catal. 2013, 3, 2856.
[1]
(c) Du, Z.-T.; Shao, Z.-H. Chem. Soc. Rev. 2013, 42, 1337.
[1]
(d) Pellissier, H. Adv. Synth. Catal. 2020, 362, 2289.
[1]
(e) Chakraborty, N.; Das, B.; Rajbongshi, K. K.; Patel, B. K. Eur. J. Org. Chem. 2022, 2022, e202200273.
[2]
Zhou, J. Multicatalyst System in Asymmetric Catalysis, John Wiley & Sons, New York, 2014.
[3]
(a) Bredig, G.; Fiske, P. S. Biochem. Z. 1912, 46, 7.
[3]
(b) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
[4]
(a) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 7, 5239.
[4]
(b) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024.
[4]
(c) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008.
[4]
(d) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1998.
[5]
(a) Chen, K. Q.; Arnold, F. H. Proc. Natl. Acad. Sci. 1993, 90, 5618.
[5]
(b) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, VCH, Weinheim, 1995.
[5]
(c) Voss, C. V.; Gruber, C. C.; Kroutil, W. Angew. Chem. Int. Ed. 2008, 120, 753.
[5]
(d) Marchetti, L.; Levine, M. ACS Catal. 2011, 1, 1090.
[6]
(a) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
[6]
(b) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
[6]
(c) List. B. Chem. Rev. 2007, 107, 5413.
[6]
(d) MacMillan. D. W. C. Nature 2008, 455, 304.
[7]
Peng, Y.-B.; Huo, X.-H.; Luo, Y.-C.; Wu, L.; Zhang, W.-B. Angew. Chem. Int. Ed. 2021, 60, 24941.
[8]
For reviews: (a) Zhong, C.; Shi, X.-D. Eur. J. Org. Chem. 2010, 2999.
[8]
(b) Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633.
[8]
(c) Borah, B.; Dwivedi, K. D.; Chowhan, L. R. Asian J. Org. Chem. 2021, 10, 2709.
[9]
(a) Long, J.; Ding, K.-L. Angew. Chem. Int. Ed. 2001, 40, 544.
[9]
(b) Zhou, J.; Wakchaure, V.; Kraft, P.; List, B. Angew. Chem. Int. Ed. 2008, 47, 7656.
[9]
(c) Lv, J.; Li, X.; Zhong, L.; Luo, S.-Z; Cheng, J.-P. Org. Lett. 2010, 12, 1096.
[9]
(d) Lv, J.; Zhang, L.; Zhou, Y.-M; Nie, Z.-X; Luo, S.-Z; Cheng, J.-P. Angew. Chem. Int. Ed. 2011, 50, 6610.
[9]
(e) Zeng, X.-P.; Cao, Z.-Y.; Wang, X.; Chen, L.; Zhou, F.; Zhu, F.; Wang, C.-H.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 416.
[9]
(f) Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730.
[9]
(g) Gao, X.-T.; Gan, C.-C.; Liu, S.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. ACS Catal. 2017, 7, 8588.
[9]
(h) Wu, W.-B.; Yu, X.; Yu, J.-S.; Wang, X.; Wang, W.-G.; Zhou, J. CCS Chem. 2021, 3, 2168.
[9]
(i) Zhang, Z.; Zhang, Z.-H.; Zhou, F.; Zhou, J. Org. Lett. 2021, 23, 2726.
[10]
(a) Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222.
[10]
For selected examples: (b) Longmire, J.; Wang, B.; Zhang, X.-M. J. Am. Chem. Soc. 2002, 124, 13400.
[10]
(c) Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem. Int. Ed. 2006, 45, 1979.
[10]
(d) Yan, X.-X.; Peng, Q.; Li, Q.; Zhang, K.; Yao, J.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem. Soc. 2008, 130, 14362.
[10]
(e) Xu, H.; Zuend, S. J.; Woll, M. J.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986.
[10]
(f) Beletskaya, I. P.; Nájera, C.; Yus, M. Chem. Rev. 2018, 118, 5080.
[11]
(a) Shao, Z.-H.; Zhang, H. B. Chem. Soc. Rev. 2009, 38, 2745.
[11]
(b) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365.
[12]
(a) Chen, G.-S.; Deng, Y.-J.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567.
[12]
(b) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329.
[13]
(a) Ibrahem, I.; Córdova, A. Angew. Chem. Int. Ed. 2006, 45, 1952.
[13]
(b) Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
[13]
(c) Yang, T.; Ferrali, A.; Sladojevich, F.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 9140.
[13]
(d) Li, B.-L; Liu, R.-R.; Liang, R.-X.; Jia, Y.-X. Acta Chim. Sinica 2017, 75, 448. (in Chinese).
[13]
(李保乐, 刘人荣, 梁仁校, 贾义霞, 化学学报, 2017, 75, 448.)
[13]
(e) Nair, V. V.; Arunprasath, D.; Pandidurai, S.; Sekar, G. Eur. J. Org. Chem. 2022, 2022, e202200244.
[13]
(g) Nielsen, C. D.-T.; Linfoot, J. D.; Williamsa, A. F.; Spivey, A. C. Org. Biomol. Chem. 2022, 20, 2764.
[14]
(a) Klussmann, M. Angew. Chem. Int. Ed. 2009, 48, 7124.
[14]
(b) Ren, L.; Lei, T.; Ye, J.-X.; Gong, L.-Z. Angew. Chem., nt. Ed. 2012, 51, 771.
[14]
(c) Wu, X.; Li, M.-L.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 1091. (in Chinese).
[14]
(吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.)
[14]
(d) Yang, Z.-P.; Zhang, W.; You, S.-L. J. Org. Chem. 2014, 79, 7785.
[14]
(e) Fang, G.-C.; Cheng, Y.-F.; Yu, Z.-L.; Li, Z.-L.; Liu, X.-Y. Top. in Current Chemistry 2019, 23.
[15]
(a) Lebeuf, R. I.; Hirano, K.; Glorius, F. Org. Lett. 2008, 10, 4243.
[15]
(b) Cardinal-David, B.; Raup, D. E. A.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345.
[15]
(c) Raup, D. E. A.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766.
[15]
(d) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
[15]
(e) Wang, A.; Xiao, Y.-L.; Zhou, Y.; Xu, J.-Y.; Liu, H. Chin. J. Org. Chem. 2017, 37, 2590. (in Chinese).
[15]
(王翱, 肖永龙, 周宇, 徐进宜, 柳红, 有机化学, 2017, 37, 2590.)
[15]
(f) Song, J.; Zhang, Z.-J.; Chen, S.-S.; Fan, T.; Gong, L.-Z. J. Am. Chem. Soc. 2018, 140, 3177.
[15]
(g) Zhang, B.; Yang, G.-M.; Guo, D.-H.; Wang, J. Org. Chem. Front. 2022, 9, 5016.
[16]
(a) Arndtsen, B. A.; Gong L.-Z. Asymmetric Organocatalysis Combined with Metal Catalysis, Springer, Berlin, 2020.
[16]
(b) Gong, L.-Z. Asymmetric Organo-Metal Catalysis: Concepts, Principles, and Applications, Wiley-VCH: Weinheim, 2021.
[16]
(c) Zhang, M.-M.; Luo, Y.-Y.; Lu, L.-Q.; Xiao, W.-J. Acta Chim. Sinica 2018, 76, 838. (in Chinese).
[16]
(张毛毛, 骆元元, 陆良秋, 肖文精, 化学学报, 2018, 76, 838.)
[16]
(d) Tian, F.; Zhang, J.; Yang, W.-L.; Deng, W.-P. Chin. J. Org. Chem. 2020, 40, 3262. (in Chinese).
[16]
(田飞, 张键, 杨武林, 邓卫平, 有机化学, 2020, 40, 3262.)
[16]
(e) Bao, M.; Zhou, S.; Hu, W.-H.; Xu, X.-F. Chin. Chem. Lett. 2022, 33, 4969.
[16]
(f) Del Vecchio, A.; Sinibaldi, A.; Nori, V.; Giorgianni, G.; Di Carmine, G.; Pesciaioli, F. Chem. Eur. J. 2022, DOI: 10.1002/chem.202200818.
[17]
(a) Xu, X.-F.; Zhou, J.; Yang, L.-P.; Hu, W.-H. Chem. Commun. 2008, 6564.
[17]
(b) Hu, W.-H.; Xu, X.-F.; Zhou, J.; Liu, W.-J.; Huang, H.-X.; Hu, J.; Yang, L.-P.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782.
[17]
(c) Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nat. Chem. 2012, 4, 733.
[18]
Cai, Q.; Zhao, Z.-A.; You, S.-L. Angew. Chem. Int. Ed. 2009, 48, 7428.
[19]
(a) Han, Z.-Y.; Xiao, H.; Chen, X.-H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182.
[19]
(b) Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204.
[20]
Yin, X.-P.; Zeng, X.-P.; Liu, Y.-L.; Liao, F.-M.; Yu, J.-S.; Zhou, F.; Zhou, J. Angew. Chem. Int. Ed. 2014, 53, 13740.
[21]
Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
[22]
Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416.
[23]
(a) Schwemberger, W.; Gordon, W.; Chem. Zentralbl. 1935, 106, 514.
[23]
(b) Gassman, P. G.; Meyer, G.; Williams, F. J. J. Am. Chem. Soc. 1972, 94, 7741.
[23]
(c) Norman, R. O. C.; Parr, W. J. E.; Thomas, C. B. J. Chem. Soc. Perkin Trans. 1 1976, 1983.
[23]
(d) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285.
[24]
Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415.
[25]
Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
[26]
(a) Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766.
[26]
(b) Alcaide, B.; Almendros, P.; Alonso, J. M. Molecules 2011, 16, 7815.
[26]
(c) Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448.
[26]
(d) Barbour, P. M.; Marholz, L. J.; Chang, L.; Xu, W.; Wang, X. Chem. Lett. 2014, 43, 572.
[26]
(e) Fensterbank, L.; Malacria, M. Acc. Chem. Res. 2014, 47, 953.
[26]
(f) Füerstner, A. Angew. Chem., Int. Ed. 2014, 53, 8587.
[26]
(g) Füerstner, A. Acc. Chem. Res. 2014, 47, 925.
[26]
(h) Zhang, Y.; Luo, T.; Yang, Z. Nat. Prod. Rep. 2014, 31, 489.
[26]
(i) Pflästerer, D.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 1331.
[27]
Early review of organo/Au cooperative catalysis: (a) Loh, C. C. J.; Ender, D. Chem. Eur. J. 2012, 18, 10212.
[27]
Recent review of chiral organo/Au cooperative catalysis for alkyne functionalization: (b) Bao, M.; Zhou, S.; Hu, W.-H.; Xu, X.-F. Chin. Chem. Lett. 2022, 33, 4969.
[28]
(a) Zhou, J. Chem. Asian J. 2010, 5, 422.
[28]
(b) Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211.
[29]
(a) Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 121, 9085.
[29]
(b) Khin, C.; Hashmi, A. S. K. Rominger, F. Eur. J. Inorg. Chem. 2010, 1063.
[30]
Zweifel, T.; Hollmann, D.; Prüger, B.; Nielsen, M.; Jørgensen. K. A. Tetrahedron: Asymmetry 2010, 21, 1624.
[31]
Wu, X.; Li, M.-L.; Chen, D. F.; Chen, S.-S. J. Org. Chem. 2014, 79, 4743.
[32]
Hack, D.; Loh, C. C. J.; Hartmann, J. M.; Raabe, G.; Enders, D. Chem. Eur. J. 2014, 20, 3917.
[33]
Loh, C. C. J.; Badorrek, J.; Raabe, G.; Enders, D. Chem. Eur. J. 2011, 17, 13409.
[34]
(a) Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem. Int. Ed. 2009, 48, 8923.
[34]
(b) Belot, S.; Quintard, A.; Krause, N.; Alexakis, A. Adv. Synth. Catal. 2010, 352, 667.
[35]
You, Z.-H.; Chen, Y.-H.; Wu, X.-N.; Liu, Y.-K. Adv. Synth. Catal. 2017, 359, 4260.
[36]
Chiarucci, M.; di Lillo, M.; Romaniello, A.; Cozzi, P. G.; Cera, G.; Bandini, M. Chem. Sci. 2012, 3, 2859.
[37]
Ballesteros, A.; Morán-Poladura, P.; González, J. M. Chem. Commun. 2016, 52, 2905.
[38]
Jensen, K. L.; Franke, P. T.; Arrniz, C.; Kobbelgaard, S.; Jørgensen, K. A. Chem. Eur. J. 2010, 16, 1750.
[39]
Yu, C.-G.; Ji, P.; Zhang, Y.-T.; Meng, X.; Wang, W. Org. Lett. 2021, 23, 7656.
[40]
Genet, M.; Takfaoui, A.; Marrot, J.; Greck, C.; Moreau, X. Adv. Synth. Catal. 2021, 363, 4516.
[41]
Monge, D.; Jensen, K. L.; Franke, P. T.; Lykke, L.; Jørgensen, K. A. Chem. Eur. J. 2010, 16, 9478.
[42]
Chen, X.-J.; Chen, H.; Ji, X.; Jiang, H.-L.; Yao, Z.-J.; Liu, H. Org. Lett. 2013, 15, 1846.
[43]
Barber, D. M.; Sanganee, H. J.; Dixon, D. J. Org. Lett. 2012, 14, 5290.
[44]
Barber, D. M.; D?uriš, A.; Thompson, A. L.; Sanganee, H. J.; Dixon, D. J. ACS Catal. 2014, 4, 634.
[45]
Urban, M.; Nigríni, M.; Císařová, I.; Veselý, J. J. Org. Chem. 2021, 86, 18139.
[46]
Guo, W.-G.; Li, L.; Ding, Q.; Lin, X.-F.; Liu, X.-H.; Wang, K.; Liu, Y.; Fan, H.-J.; Li, C. ACS Catal. 2018, 8, 10180.
[47]
(a) Saito, H.; Iwai, R.; Uchiyama, T.; Miyake, M.; Miyairi, S. Chem. Pharm. Bull. 2010, 58, 872.
[47]
(b) Terada, M.; Toda, Y. Angew. Chem., nt. Ed. 2012, 51, 2093.
[47]
(c) Guo, X.; Hu, W.-H. Acc. Chem. Res. 2013, 46, 2427.
[47]
(d) Chen, D.-F.; Wu, P.-Y.; Gong, L.-Z. Org. Lett. 2013, 15, 3958.
[47]
(e) Meng, X.-L.; Yang, B.-M.; Zhang, L.-X.; Pan, G.-Y.; Zhang, X.-H.; Shao, Z.-H. Org. Lett. 2019, 21, 1292.
[48]
Ho, T.-L. Chem. Rev. 1975, 75, 1.
[49]
Fructos, M. R.; Beldrrain, T. R.; de Frémont, P.; Scott, N. M.; Nolan, S. P.; Díaz-Requejo, M. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284.
[50]
Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 11916.
[51]
Cao, Z.-Y.; Zhao, Y.-L.; Zhou, J. Chem. Commun. 2016, 52, 2537.
[52]
Zhao, Y.-L.; Cao, Z.-Y.; Zeng, X.-P.; Shi, J.-M.; Yu, Y.-H.; Zhou, J. Chem. Commun. 2016, 52, 3943.
[53]
Liao, F.-M.; Du, Y.; Zhou, F.; Zhou, J. Acta Chim. Sinica 2018, 76, 862. (in Chinese).
[53]
(廖富民, 杜溢, 周锋, 周剑, 化学学报, 2018, 76, 862.)
[54]
Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem. Int. Ed. 2017, 56, 2459.
[55]
Annaka, M.; Yasuda, K.; Yamada, M.; Kawai, A.; Takamura, N.; Sugasawa, S.; Matsuoka, Y.; Iwata, H.; Fukushima, T. Heterocycles 1994, 39, 251.
[56]
Cui, X.-Y.; Zhao, Y.-L.; Chen, Y.-M.; Dong, S.-Z.; Zhou, F.; Wu, H. -H.; Zhou, J. Org. Lett. 2021, 23, 4864.
[57]
Dong, G.-Z.; Bao, M.; Xie, X.-D.; Jia, S.-K.; Hu, W.-H.; Xu, X.-F. Angew. Chem. Int. Ed. 2021, 60, 1992.
Options
文章导航

/

〈 〉