基于分子容器的有机阳离子受体研究进展

doi:10.6023/cjoc202303028

摘要/Abstract

分子容器是一种可以模仿酶的受限空间以及活性位点的超分子结构, 自从出现以来引起了超分子科学家的广泛兴趣. 科学家们开发了具有不同大小及电性的分子容器, 以期望其在反应中间体稳定、活性物种捕获以及催化反应等领域具有应用价值. 主要综述了超分子领域广泛关注的几种作为阳离子受体的分子容器, 它们通过对阳离子物种的包裹从而实现稳定活性物种、调节反应活性以及提升底物/反应选择性的目的. 以分子容器的功能分类, 对分子容器的识别行为及其对阳离子物种性质的调控功能进行总结, 阐释其中的原理和规律并对该领域未来的发展进行展望.

关键词: 受限空间, 分子容器, 自组装, 有机阳离子, 催化

Molecular containers are supramolecular structures that mimic the confined space and active sites of enzymes, attracting broad interest of supramolecular scientists since their emergence. Scientists have developed molecular containers with different sizes and electronic properties, hoping that they can be applied in stabilizing reaction intermediates, capturing active species and catalyzing reactions. A number of representative molecular containers that are widely studied as cation receptors in the supramolecular field are reviewed. They possess the properties of stabilizing active species, regulating reaction activity and enhancing substrate/reaction selectivity by encapsulating cationic species. The recognition behavior of molecular containers and their function of regulating the properties of cationic species are summarized. The principles and rules involved are explained and an outlook on the future development of this field is provided.

Key words: confined space, molecular container, self-assembly, organic cation, catalysis

引用此文

朱文杰, 徐振创, 顾玉诚, 赵延川. 基于分子容器的有机阳离子受体研究进展[J]. 有机化学, 2023, 43(9): 2991-3005.

Wenjie Zhu, Zhenchuang Xu, Yu-Cheng Gu, Yanchuan Zhao. Research Progress on Organic Cation Receptors Based on Molecular Containers[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 2991-3005.

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图/表 23

图1. 代表性的基于分子容器的有机阳离子受体

图式1. 通过分子容器稳定?鎓离子

Scheme 1. Stabilization of tropylium via encapsulation with molecular container

图式2. 利用分子容器稳定亚胺正离子和鏻/酮加合物

Scheme 2. Stabilization of iminium and phosphonium/ketone adduct using molecular containers

图式3. 利用CB[7]稳定的质子泵抑制剂

Scheme 3. Stabilization of proton-pump inhibitor with CB[7]

图式4. 利用CB[7]稳定自由基阳离子

Scheme 4. Stabilization of radical cations with CB[7]

图式5. 四面体分子容器催化的环化反应

Scheme 5. Cyclization reaction catalyzed by a tetrahedral molecular container

图式6. 四面体分子容器催化的氮杂-Prins环化

Scheme 6. Azo-Prins cyclization catalyzed by a tetrahedral molecular container

图式7. 四面体分子容器促进的Nazarov环化

Scheme 7. Nazarov cyclization promoted by a tetrahedral molecular container

图式8. 四面体分子容器促进的原甲酸酯水解

Scheme 8. Orthoformate hydrolysis promoted by a tetrahedral molecular container

图式9. 四面体分子容器催化的氮杂-Darzens环化反应

Scheme 9. Azo-darzens cyclization catalyzed by a tetrahedral molecular container

图式10. 氢键组装型分子容器催化的成萜环化反应

Scheme 10. Terpene cyclization catalyzed by a hydrogen bonded molecular container

图式11. 氢键组装型分子容器促进的缩醛水解

Scheme 11. Acetal hydrolysis promoted by a hydrogen bonded molecular container

图式12. 利用氢键组装型分子容器促进不对称氢化

Scheme 12. Asymmetric hydrogenation promoted by a hydrogen bonded molecular container

图式13. 利用四面体分子容器促进的醛和醚的碳氢键活化

Scheme 13. C—H bonds of aldehydes and ethers promoted by a tetrahedral molecular container

图式14. 四面体分子容器促进的烯烃异构化

Scheme 14. Olefin isomerization promoted by a tetrahedral molecular container

图式15. 四面体分子容器介导的烯烃选择性催化氢化

Scheme 15. Selective olefin hydrogenation mediated by a tetrahedral molecular container

图式16. 四面体分子容器催化的氢烷氧基化

Scheme 16. Hydroalkoxylation catalyzed by a tetrahedral molecular container

图式17. 酶催化酯水解和金属催化氢烷氧基化串联反应

Scheme 17. Tandem esterase-catalyzed ester hydrolysis and metal-catalyzed hydroalkoxylation

图式18. 四面体分子容器介导的还原消除

Scheme 18. Reductive elimination mediated by a tetrahedral molecular container

图式19. 基于氢键组装型分子容器调控光反应催化活性

Scheme 19. Regulation of the catalytic activity of a photoreaction based on a hydrogen-bonded molecular container

图式20. 氢键组装型分子容器介导的末端炔烃水合反应

Scheme 20. Hydration of terminal alkynes mediated by a hydrogen bonded molecular container

图式21. 基于氢键组装型分子容器调控双核金配合物催化活性

Scheme 21. Regulation of the activity of binuclear gold complexes with a hydrogen-bonded molecular container

图式22. CB[8]介导的铜催化不对称Diels-Alder反应

Scheme 22. Copper-catalyzed asymmetric Diels-Alder reaction mediated by CB[8]

参考文献 100

[1]	Wilson A. J. Annu. Reports Prog. Chem. Sect. B: Org. Chem. 2007, 103, 174.
[2]	Sherman J. C.; Cram D. J. J. Am. Chem. Soc. 1989, 111, 4527. doi: 10.1021/ja00194a074
[3]	Psilbu S.; Wiberg N.; Schuster H. Angew. Chem., nt. Ed. 1991, 97, 1024.
[4]	Chapman O. L.; Mcintosh C. L.; Pacansky J. J. Am. Chem. Soc. 1973, 95, 614. doi: 10.1021/ja00783a066
[5]	Warmuth R. Angew. Chem., nt. Ed. 1997, 36, 1347.
[6]	Warmuth R. Chem. Commun. 1998, 59.
[7]	Warmuth R.; Marvel M. A. Chem.-Eur. J. 2001, 7, 1209. pmid: 11322547
[8]	Roach P.; Warmuth R. Angew. Chem., nt. Ed. 2003, 42, 3039.
[9]	Liu X.-J.; Chu G.-S.; Moss R. A., Sauers R. R.; Warmuth R. Angew. Chem., nt. Ed. 2005, 44, 1994.
[10]	Hooley R. J.; Iwasawa T.; Rebek J. J. Am. Chem. Soc. 2007, 129, 15320.
[11]	Butterfield S. M.; Rebek J. Chem. Commun. 2007, 1605.
[12]	Xu L.-N.; Hua S.-G.; Li S.-H. Chem. Commun. 2013, 49, 1542. doi: 10.1039/c2cc38165f
[13]	Restorp P.; Rebek J. J. Am. Chem. Soc. 2008, 130, 11850. doi: 10.1021/ja803854r pmid: 18698780
[14]	Hou J.-L.; Ajami D.; Rebek J. J. Am. Chem. Soc. 2008, 130, 7810. doi: 10.1021/ja802288k
[15]	Körner S. K.; Tucci F. C.; Rudkevich D. M.; Heinz T.; Rebek J. Chem.-Eur. J. 2000, 6, 187. pmid: 10747403
[16]	Fujita M.; Oguro D.; Miyazawa M.; Oka H.; Yamaguchi K.; Ogura K. Nature 1995, 378, 469. doi: 10.1038/378469a0
[17]	Yoshizawa M.; Kusukawa T.; Fujita M.; Yamaguchi K. J. Am. Chem. Soc. 2000, 122, 6311. doi: 10.1021/ja000779c
[18]	Yoshizawa M.; Kusukawa T.; Fujita M.; Sakamoto S.; Yamaguchi K. J. Am. Chem. Soc. 2001, 123, 10454. pmid: 11673975
[19]	Horiuchi S.; Murase T.; Fujita M. J. Am. Chem. Soc. 2011, 133, 12445. doi: 10.1021/ja205450a
[20]	Greenaway R. L.; Holden D.; Eden E. G. B.; Stephenson A.; Yong C. W.; Bennison M. J.; Hasell T.; Briggs M. E.; James S. L.; Cooper A. I. Chem. Sci. 2017, 8, 2640. doi: 10.1039/c6sc05196k pmid: 28553499
[21]	Turega S.; Whitehead M.; Hall B. R.; Haddow M. F.; Hunter C. A.; Ward M. D. Chem. Commun. 2012, 48, 2752. doi: 10.1039/c2cc17369g
[22]	Webber M. J.; Langer R. Chem. Soc. Rev. 2017, 46, 6600. doi: 10.1039/C7CS00391A
[23]	Brown C. J.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2009, 131, 17530. doi: 10.1021/ja906386w
[24]	Hart-Cooper W. M.; Zhao C.; Triano R. M.; Yaghoubi P.; Ozores H. L.; Burford K. N.; Toste F. D.; Bergman R. G.; Raymond K. N. Chem. Sci. 2015, 6, 1383. doi: 10.1039/c4sc02735c pmid: 29560226
[25]	Galan A.; Ballester P. Chem. Soc. Rev. 2016, 45, 1720. doi: 10.1039/C5CS00861A
[26]	Brown C. J.; Toste F. D.; Bergman R. G.; Raymond K. N. Chem. Rev. 2015, 115, 3012. doi: 10.1021/cr4001226
[27]	Mouarrawis V.; Plessius R.; van der Vlugt J. I.; Reek J. N. H. Front. Chem. 2018, 6, 623. doi: 10.3389/fchem.2018.00623
[28]	Wu L.; Chen Y.-S.; Pei J.-F.; Tang M.; Wang S.-S.; Liu Z.-C. Chin. J. Chem. 2019, 37, 834. doi: 10.1002/cjoc.v37.8
[29]	Xu Z.-C.; Fang N.; Zhao Y.-C. J. Am. Chem. Soc. 2021, 143, 3162. doi: 10.1021/jacs.0c12223
[30]	Assaf K. I.; Nau W. M. Chem. Soc. Rev. 2015, 44, 394. doi: 10.1039/C4CS00273C
[31]	Mock W. L.; Irra T. A.; Wepsiec J. P.; Manimaran T. L. J. Org. Chem. 1983, 48, 3619. doi: 10.1021/jo00168a070
[32]	Decomposition C.; Takaya H.; Science M.; Hirao K.; Promoted S.; Available S. M.; Mock W. L.; Wepsiec J. P.; Adhya M. J. Org. Chem. 1989, 54, 5302. doi: 10.1021/jo00283a024
[33]	Finbloom J. A.; Han K.; Slack C. C.; Furst A. L.; Francis M. B. J. Am. Chem. Soc. 2017, 139, 9691. doi: 10.1021/jacs.7b05164 pmid: 28650616
[34]	Brevø T. G.; Filius M.; Araman C.; Van Der Helm M. P.; Hagedoorn P.; Joo C.; Van Kasteren S. I.; Eelkema R. Angew. Chem., nt. Ed. 2020, 59, 9340.
[35]	Jiao Y.; Tang B.-H.; Zhang Y.-C.; Xu J. F.; Wang Z.-Q.; Zhang X. Angew. Chem., nt. Ed. 2018, 57, 6077.
[36]	Cong H.; Yamato T.; Tao Z. J. Mol. Catal. A: Chem. 2013, 379, 287. doi: 10.1016/j.molcata.2013.08.025
[37]	Koner A. L.; Márquez C.; Dickman M. H.; Nau W. M. Angew. Chem., nt. Ed. 2011, 50, 545.
[38]	Zheng L.-F.; Sonzini S.; Ambarwati M.; Rosta E.; Scherman O. A.; Herrmann A. Angew. Chem., nt. Ed. 2015, 54, 13007.
[39]	De Lima S. M.; Gómez J. A.; Barros V. P.; Vertuan G. D. S.; Assis M. D. D.; Graeff C. F. D. O.; Demets G. J. F. Polyhedron 2010, 29, 3008. doi: 10.1016/j.poly.2010.08.001
[40]	Gong W.-J.; Ma J.; Zhao Z.-Y.; Gao F.; Liang F.; Zhang H.-J.; Liu S.-M. J. Org. Chem. 2017, 82, 3298. doi: 10.1021/acs.joc.6b02971
[41]	Eelkema R.; Maeda K.; Odell B.; Anderson H. L. J. Am. Chem. Soc. 2007, 129, 12384. pmid: 17887677
[42]	Liu Y.; Shi J.; Chen Y.; Ke C.-F. Angew. Chem., nt. Ed. 2008, 47, 7293.
[43]	Zhang G.-W.; Li P.-F.; Meng Z.; Wang H.-X.; Han Y.; Chen C.-F. Angew. Chem.,Int. Ed. 2016, 55, 5304. doi: 10.1002/anie.v55.17
[44]	Han X.-N.; Li P.-F.; Han Y.; Chen C.-F. Angew. Chem.,Int. Ed. 2022, 61, e202202527. doi: 10.1002/anie.v61.21
[45]	Zhu D.-S.; Sun B.; Tong L.; Wu Y.-T.; Cetin M. M.; Li H. Org. Lett. 2022, 24, 8980. doi: 10.1021/acs.orglett.2c03560
[46]	Black S. P.; Sanders J. K. M.; Stefankiewicz A. R. Chem. Soc. Rev. 2014, 43, 1861. doi: 10.1039/C3CS60326A
[47]	Corbett P. T.; Sanders J. K. M.; Otto S. J. Am. Chem. Soc. 2005, 127, 9390. pmid: 15984865
[48]	Corbett P. T.; Tong L. H.; Sanders J. K. M.; Otto S. J. Am. Chem. Soc. 2005, 127, 8902. pmid: 15969538
[49]	Brisig B.; Sanders J. K. M.; Otto S. Angew. Chem.,Int. Ed. 2003, 42, 1270. doi: 10.1002/anie.200390326
[50]	James L. I.; Beaver J. E.; Rice N. W.; Waters M. L. J. Am. Chem. Soc. 2013, 135, 6450. doi: 10.1021/ja307907p
[51]	Cram D. J.; Karbach S.; Kim Y. H.; Baczynskyj L.; Kalleymeyn G. W. J. Am. Chem. Soc. 1985, 107, 2575. doi: 10.1021/ja00294a076
[52]	MacGillivray L. R.; Atwood J. L. Nature 1997, 389, 469. doi: 10.1038/38985
[53]	Avram L.; Cohen Y. J. Am. Chem. Soc. 2002, 124, 15148. pmid: 12487570
[54]	La Manna P.; Talotta C.; Floresta G.; De Rosa M.; Soriente A.; Rescifina A.; Gaeta C.; Neri P. Angew. Chem.,Int. Ed. 2018, 57, 5423. doi: 10.1002/anie.v57.19
[55]	Bräuer T. M.; Zhang Q.; Tiefenbacher K. Angew. Chem., nt. Ed. 2016, 55, 7698.
[56]	Bräuer T. M.; Zhang Q.; Tiefenbacher K. J. Am. Chem. Soc. 2017, 139, 17500. doi: 10.1021/jacs.7b08976
[57]	Jans A. C. H.; Gómez-Suárez A.; Nolan S. P.; Reek J. N. H. Chem.-Eur. J. 2016, 22, 14836. doi: 10.1002/chem.v22.42
[58]	Cavarzan A.; Scarso A.; Sgarbossa P.; Strukul G.; Reek J. N. H. J. Am. Chem. Soc. 2011, 133, 2848. doi: 10.1021/ja111106x
[59]	Caneva T.; Sperni L.; Strukul G.; Scarso A. RSC Adv. 2016, 6, 83505. doi: 10.1039/C6RA20271C
[60]	Shivanyuk A.; Friese J. C.; Döring S.; Rebek J. J. Org. Chem. 2003, 68, 6489. doi: 10.1021/jo034791+
[61]	Heinz T.; Rudkevich D. M.; Rebek J. Nature 1998, 394, 764. doi: 10.1038/29501
[62]	Chwastek M.; Cmoch P.; Szumna A. J. Am. Chem. Soc. 2022, 144, 5350. doi: 10.1021/jacs.1c11793 pmid: 35274940
[63]	Tang M.; Liang Y.-M.; Lu X.-Y.; Miao X.-H.; Jiang L.; Liu J.-L; Bian L.-F.; Wang S.-S.; Wu L.; Liu Z.-C. Chem 2021, 7, 2160. doi: 10.1016/j.chempr.2021.05.004
[64]	Brumaghim J. L.; Michels M.; Raymond K. N. Eur. J. Org. Chem. 2004, 4552.
[65]	Dong V. M.; Fiedler D.; Carl B.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2006, 128, 14464. pmid: 17090022
[66]	Pluth M. D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2007, 129, 11459. doi: 10.1021/ja072654e
[67]	Hastings C. J.; Pluth M. D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2010, 132, 6938. doi: 10.1021/ja102633e
[68]	Hastings C. J.; Fiedler D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2008, 130, 10977. doi: 10.1021/ja8013055
[69]	Dalton D. M.; Ellis S. R.; Nichols E. M.; Mathies R. A.; Toste F. D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2015, 137, 10128. doi: 10.1021/jacs.5b06317 pmid: 26256754
[70]	Shivanyuk A.; Paulus E. F.; Böhmer V. Angew. Chem., nt. Ed. 1999, 38, 2906.
[71]	Li Y.; Duan Y.-M.; Chen G.-H.; Hu H.-R.; Han X.-N.; Wang K.-P.; Hu Z.-Q.; Chen C.-F. Org. Lett. 2023, 25, 364. doi: 10.1021/acs.orglett.2c04077
[72]	Brumaghim J. L.; Michels M.; Pagliero D.; Raymond K. N. Eur. J. Org. Chem. 2004, 2004, 5115. doi: 10.1002/ejoc.v2004:24
[73]	Saleh N.; Koner A. L.; Nau W. M. Angew. Chem., nt. Ed. 2008, 47, 5398.
[74]	Shi J.; Chen Y.; Wang Q.; Liu Y. Adv. Mater. 2010, 22, 2575. doi: 10.1002/adma.v22:23
[75]	Hart-Cooper W. M.; Clary K. N.; Toste F. D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2012, 134, 17873. doi: 10.1021/ja308254k pmid: 23066637
[76]	Kaphan D. M.; Toste F. D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2015, 137, 9202. doi: 10.1021/jacs.5b01261 pmid: 26176416
[77]	Miyamura H.; Bergman R. G.; Raymond K. N.; Toste F. D. J. Am. Chem. Soc. 2020, 142, 19327. doi: 10.1021/jacs.0c09556
[78]	Pluth M. D.; Bergman R. G. Science 2007, 316, 85. doi: 10.1126/science.1138748
[79]	Pluth M. D.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2008, 130, 11423. doi: 10.1021/ja802839v
[80]	Pluth M. D.; Bergman R. G.; Raymond K. N. Angew. Chem., nt. Ed. 2007, 46, 8587.
[81]	Bierschenk S. M.; Bergman R. G.; Raymond K. N.; Toste F. D. J. Am. Chem. Soc. 2020, 142, 733. doi: 10.1021/jacs.9b13177 pmid: 31909615
[82]	Zhang Q.; Tiefenbacher K. Nat. Chem. 2015, 7, 197. doi: 10.1038/nchem.2181 pmid: 25698327
[83]	Zhang Q.; Catti L.; Pleiss J.; Tiefenbacher K. J. Am. Chem. Soc. 2017, 139, 11482. doi: 10.1021/jacs.7b04480 pmid: 28590723
[84]	Sokolova D.; Piccini G.; Tiefenbacher K. Angew. Chem., nt. Ed. 2022, 61, e202203384.
[85]	Zhang Q.; Rinkel J.; Goldfuss B.; Dickschat J. S.; Tiefenbacher K. Nat. Catal. 2018, 1, 609. doi: 10.1038/s41929-018-0115-4 pmid: 30221250
[86]	Zhang Q.; Tiefenbacher K. Angew. Chem., nt. Ed. 2019, 58, 12688.
[87]	Zhang Q.; Tiefenbacher K. J. Am. Chem. Soc. 2013, 135, 16213. doi: 10.1021/ja4080375 pmid: 24131349
[88]	Köster J. M.; Tiefenbacher K. ChemCatChem 2018, 10, 2941. doi: 10.1002/cctc.v10.14
[89]	MacMillan D. W. C. Nature 2008, 455, 304. doi: 10.1038/nature07367
[90]	Leung D. H.; Fiedler D.; Bergman R. G.; Raymond K. N. Angew. Chem., nt. Ed. 2004, 43, 963.
[91]	Leung D. H.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2006, 128, 9781. doi: 10.1021/ja061412w
[92]	Leung D. H.; Bergman R. G.; Raymond K. N. J. Am. Chem. Soc. 2007, 129, 2746. doi: 10.1021/ja068688o
[93]	Bender T. A.; Bergman R. G.; Raymond K. N.; Toste F. D. J. Am. Chem. Soc. 2019, 141, 11806. doi: 10.1021/jacs.9b05604
[94]	Wang Z. J.; Brown C. J.; Bergman R. G.; Raymond K. N.; Toste F. D. J. Am. Chem. Soc. 2011, 133, 7358. doi: 10.1021/ja202055v
[95]	Wang Z. J.; Clary K. N.; Bergman R. G.; Raymond K. N.; Toste F. D. Nat. Chem. 2013, 5, 100. doi: 10.1038/nchem.1531
[96]	Levin M. D.; Kaphan D. M.; Hong C. M.; Bergman R. G.; Raymond K. N.; Toste F. D. J. Am. Chem. Soc. 2016, 138, 9682. doi: 10.1021/jacs.6b05442 pmid: 27458778
[97]	Kaphan D. M.; Levin M. D.; Bergman R. G.; Raymond K. N.; Toste F. D. Science 2015, 350, 1235. doi: 10.1126/science.aad3087 pmid: 26785485
[98]	Bender T. A.; Morimoto M.; Bergman R. G.; Raymond K. N.; Toste F. D. J. Am. Chem. Soc. 2019, 141, 1701. doi: 10.1021/jacs.8b11842
[99]	Narayanam J. M. R.; Stephenson C. R. J. Chem. Soc. Rev. 2011, 40, 102. doi: 10.1039/B913880N
[100]	Bianchini G.; Scarso A.; Sorella G. L.; Strukul G. Chem. Commun. 2012, 48, 12082. doi: 10.1039/c2cc37374b