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Journal of the American Chemical Society
10. Zheng, C.; You, S. L. Transfer hydrogenation with Hantzsch esters
and related organic hydride donors. Chem. Soc. Rev. 2012, 41,
2498−2518.
11. Zhang, P.; Yuly, J. L.; Lubner, C. E.; Mulder, D. W.; King, P. W.;
Peters, J. W.; Beratan, D. N. Electron Bifurcation: Thermodynamics
and kinetics of two-electron brokering in biological redox chemistry.
Acc. Chem. Res. 2017, 50, 2410−2417.
12. Buckel, W.; Thauer, R. K. Flavin-based electron bifurcation, a new
mechanism of biological energy coupling. Chem. Rev. 2018, 118,
3862−3886.
13. Cook, T. R.; Stang, P. J. Recent developments in the preparation and
chemistry of metallacycles and metallacages via coordination. Chem.
Rev. 2015, 115, 7001−7045.
ASSOCIATED CONTENT
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Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website.
Complete experimental details and supporting Figures.
X-ray data for Zn−FPB (CCDC 1891712);
X-ray data for Zn−FPB ⊃ 1 (CCDC 1891711);
X-ray data for Fe−FPB (CCDC 1891710);
X-ray data for Co−FPB (CCDC 1891708);
X-ray data for Ni−FPB (CCDC 1891709);
X-ray data for Ni−FMB (CCDC 1906243);
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14. Brown, C. J.; Toste, F. D.; Bergman, R. G.; Raymond, K. N.
Supramolecular catalysis in metal-ligand cluster hosts. Chem. Rev.
2015, 115, 3012−3035.
15. Jiao, J.; Tan, C.; Li, Z.; Liu, Y.; Han, X.; Cui, Y., Design and
Assembly of Chiral Coordination Cages for Asymmetric Sequential
Reactions. J. Am. Chem. Soc. 2018, 140, 2251−2259.
16. Ward, M. D.; Hunter, C. A.; Williams, N. H., Coordination Cages
Based on Bis(pyrazolylpyridine) Ligands: Structures, Dynamic
Behavior, Guest Binding, and Catalysis. Acc. Chem. Res. 2018, 51,
2073−2082.
17. Zhao, L.; Jing, X.; Li, X.; Guo, X.; Zeng, L.; He, C.; Duan, C.,
Catalytic properties of chemical transformation within the confined
pockets of Werner-type capsules. Coord. Chem. Rev. 2019, 378,
151−187.
18. Jing, X.; Yang, Y.; He, C.; Chang, Z.; Reek, J. N. H.; Duan, C.
Control of redox events by dye encapsulation applied to light-driven
splitting of hydrogen sulfide. Angew. Chem. Int. Ed. 2017, 56,
11759−11763.
AUTHOR INFORMATION
Corresponding Author
*zhaol@dlut.edu.cn
*cyduan@dlut.edu.cn
ORCID
Liang Zhao: 0000-0001-8197-6686
Cheng He: 0000-0002-1426-0124
Joost N. H. Reek: 0000-0001-5024-508X
Chunying Duan: 0000-0003-1638-6633
Notes
The authors declare no competing financial interests.
19. Salles, Jr.; A. G.; Zarra, S.; Turner, R. M.; Nitschke, J. R. A self-
organizing chemical assembly line. J. Am. Chem. Soc. 2013, 135,
19143−19146.
ACKNOWLEDGMENT
20. Wang, Z. J.; Clary, K. N.; Bergman, R. G.; Raymond, K. N.; Toste,
F. D. A supramolecular approach to combining enzymatic and
transition metal catalysis. Nat. Chem. 2013, 5, 100−103.
21. Ueda, Y.; Ito, H.; Fujita, D.; Fujita, M., Permeable Self-Assembled
Molecular Containers for Catalyst Isolation Enabling Two-Step
Cascade Reactions. J. Am. Chem. Soc. 2017, 139, 6090−6093.
22. Dhers, S.; Mondal, A.; Aguilà, D.; Ramírez, J.; Vela, S.;
Dechambenoit, P.; Rouzières, M.; Nitschke, J. R.; Clérac, R.; Lehn,
J.-M. Spin state chemistry: modulation of ligand pKa by spin state
switching in a [2x2] iron(ii) grid-type complex. J. Am. Chem. Soc.
2018, 140, 8218−8227.
23. Cullen, W.; Metherell, A. J.; Wragg, A. B.; Taylor, C. G. P.;
Williams, N. H.; Ward, M. D., Catalysis in a Cationic Coordination
Cage Using a Cavity-Bound Guest and Surface-Bound Anions:
Inhibition, Activation, and Autocatalysis. J. Am. Chem. Soc. 2018,
140, 2821−2828.
This work was supported by the National Natural Science
Foundation of China (21531001, 21820102001 and
21861132004). We thank the Shenzhen HUASUAN Technology
Co., Ltd., for performing the DFT calculations and data analysis.
REFERENCES
1. Wang, D.; Astruc, D. The golden age of transfer hydrogenation.
Chem. Rev. 2015, 115, 6621−6686.
2.
3.
4.
Soldevila-Barreda, J. J.; Romero-Canelon, I.; Habtemariam, A.;
Sadler, P. J. Transfer hydrogenation catalysis in cells as a new
approach to anticancer drug design. Nat. Commun. 2015, 6, 6582.
Zhu, C.; Saito, K.; Yamanaka, M.; Akiyama, T. Benzothiazoline:
versatile hydrogen donor for organocatalytic transfer hydrogenation.
Acc. Chem. Res. 2015, 48, 388−398.
Coverdale, J. P. C.; Romero-Canelón, I.; Sanchez-Cano, C.;
Clarkson, G. J.; Habtemariam, A.; Wills, M.; Sadler, P. J.
Asymmetric transfer hydrogenation by synthetic catalysts in cancer
cells. Nat. Chem. 2018, 10, 347−354.
24. Rizzuto, F. J.; Nitschke, J. R. Stereochemical plasticity modulates
cooperative binding in a Co(II)12L6 cuboctahedron. Nat. Chem. 2017,
9, 903−908.
25. Trickett, C. A.; Osborn Popp, T. M.; Su, J.; Yan, C.; Weisberg, J.;
Huq, A.; Urban, P.; Jiang, J.; Kalmutzki, M. J.; Liu, Q.; Baek, J.;
Head-Gordon, M. P.; Somorjai, G. A.; Reimer, J. A.; Yaghi, O. M.,
Identification of the strong Brønsted acid site in a metal–organic
framework solid acid catalyst. Nat. Chem. 2019, 11, 170−176.
26. Bocokic, V.; Kalkan, A.; Lutz, M.; Spek, A. L.; Gryko, D. T.; Reek,
J. N., Capsule-controlled selectivity of a rhodium hydroformylation
catalyst. Nat. Commun. 2013, 4, 2670.
27. Cullen, W.; Takezawa, H.; Fujita, M., Demethylenation of
Cyclopropanes via Photoinduced Guest-to-Host Electron Transfer in
an M6L4 Cage. Angew. Chem. Int. Ed. 2019, 58, 9171–9173.
28. Liu, Y.; Lee, J.; Perez, L.; Gill, A. D.; Hooley, R. J.; Zhong, W.,
Selective Sensing of Phosphorylated Peptides and Monitoring
Kinase and Phosphatase Activity with a Supramolecular Tandem
Assay. J. Am. Chem. Soc. 2018, 140, 13869–13877
5.
Touge, T.; Nara, H.; Fujiwhara, M.; Kayaki, Y.; Ikariya, T. Efficient
access to chiral benzhydrolsvia asymmetric transfer hydrogenation
of unsymmetrical benzophenones with bifunctional oxo-tethered
ruthenium catalysts. J. Am. Chem. Soc. 2016, 138, 10084−10087.
Zuo, W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Amine(imine)
diphosphine iron catalysts for asymmetric transfer hydrogenation of
ketones and imines. Science 2013, 342, 1080−1083.
Zhao, M.; Yuan, K.; Wang, Y.; Li, G.; Guo, J.; Gu, L.; Hu, W.;
Zhao, H.; Tang, Z. Metal-organic frameworks as selectivity
regulators for hydrogenation reactions. Nature 2016, 539, 76−80.
Yuan, K.; Song, T.; Wang, D.; Zhang, X.; Gao, X.; Zou, Y.; Dong,
H.; Tang, Z.; Hu, W. Effective and selective catalysts for
cinnamaldehyde hydrogenation: hydrophobic hybrids of metal-
organic frameworks, metal nanoparticles, and micro- and
mesoporous polymers. Angew. Chem. Int. Ed. 2018, 57, 5708−5713.
Ilic, S.; Alherz, A.; Musgrave, C. B.; Glusac, K. D. Thermodynamic
and kinetic hydricities of metal-free hydrides. Chem. Soc. Rev. 2018,
47, 2809−2836.
6.
7.
8.
29. Shi, B.; Liu, Y.; Zhu, H.; Vanderlinden, R. T.; Shangguan, L.; Ni,
R.; Acharyya, K.; Tang, J. H.; Zhou, Z.; Li, X.; Huang, F.; Stang, P.
J., Spontaneous Formation of
a Cross-Linked Supramolecular
Polymer Both in the Solid State and in Solution, Driven by
Platinum(II) Metallacycle-Based Host-Guest Interactions. J. Am.
Chem. Soc. 2019, 141, 6494−6498.
9.
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