Abstract
By growing one metal organic frameworks (MOFs) on different metal organic frameworks plays an important role in catalytic reaction, but its cooperative catalysis in tandem reaction is an undeveloped field yet, and the reports are very limited. In this work, the material MIL-101(Cr)@MOF-867 with core–shell structure was constructed by growing MOF-867 on the ultra-stable MIL-101(Cr). The synthesized core–shell material had acid–base sites at the same time. Thus, the synergistic catalysis of deacetalization-Knoevenagel tandem reaction showed good catalytic performance and obtained ultra-high yield. In addition, all experiments showed that the core–shell catalyst MIL-101(Cr)@MOF-867 had high stability and under the same conditions, the activity remained still high after five cycles. At the same time, this is the first time to apply MIL-101(Cr)@MOF-867 catalyzing deacetalization-Knoevenagel tandem reaction.
Graphical Abstract
A bifunctional material with core–shell structure was successfully synthesized. The obtained MIL-101(Cr)@MOF-867 with both acid and base sites showed ultra-high conversion in the deacetalization-Knoevenagel tandem reaction, thanks to the Lewis acid sites catalytic deacetalization reaction provided by Cr and Zr clusters and the Brönsted base sites to catalyze Knoevenagel reaction provided by pyridine. Fortunately, after five cycles of experiments, all the characterization showed that it still maintained ultra-high catalytic performance and stability. In addition, this is the first time to catalyze the deacetalization-Knoevenagel tandem reaction by MIL-101(Cr)@MOF-867.
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References
Shi WJ, Quan YJ, Lan GX, Ni KY, Song Y, Jiang XM, Wang C, Lin WB (2021) J Am Chem Soc 143:16718–16724
He H, Sun F, Aguila B, Perman JA, Ma SQ, Zhu GS (2016) J Mater Chem A 4:15240–15246
Masoomi MY, Morsali A, Dhakshinamoorthy A, Garcia H (2019) Angew Chem Int Ed 58:15188–15205
An B, Meng YP, Li Z, Hong YH, Wang TT, Wang S, Lin JD, Wang C, Wang C, Wan SL, Wang Y, Lin WB (2019) J Catal 373:37–47
Chen YZ, Zhou YX, Wang H, Lu J, Uchida T, Xu Q, Yu SH, Jiang HL (2015) ACS Catal 5:2062–2069
Huang YB, Liang J, Wang XS, Cao R (2017) Chem Soc Rev 46:126–157
Hu Y, Zhang J, Wang Z, Huo H, Jiang Y, Xu X, Lin K (2020) ACS Appl Mater Interfaces 12:36159–36167
Gong W, Chen X, Jiang H, Chu D, Cui Y, Liu Y (2019) J Am Chem Soc 141:7498–7508
Dutta S, Kumari N, Dubbu S, Jang SW, Kumar A, Ohtsu H, Kim J, Cho SH, Kawano M, Lee IS (2020) Angew Chem 59:3416–3422
Toyao T, Saito M, Horiuchi Y, Matsuoka M (2014). Catal Sci Technol. https://doi.org/10.1039/c3cy00917c
Yang H, Fu L, Wei L, Liang J, Binks BP (2015) J Am Chem Soc 137:1362–1371
Qi L, Chen J, Zhang B, Nie R, Qi Z, Kobayashi T, Bao Z, Yang Q, Ren Q, Sun Q, Zhang Z, Huang W (2020) ACS Catal 10:5707–5714
Zhang YY, Zhou ML, Bao YS, Yang M, Cui YH, Liu DL, Wu Q, Liu L, Han ZB (2022). Mol Catal. https://doi.org/10.1016/j.mcat.2021.112068
Tang H, Yang M, Li X, Zhou ML, Bao YS, Cui YH, Zhao K, Zhang YY, Han ZB (2021) Inorg Chem Commun 123:108–368
Leng F, Liu H, Ding M, Lin QP, Jiang HL (2018) ACS Catal 8:4583–4590
Tang H, Zhou ML, Li X, Zhang YY, Han ZB (2020) ChemistrySelect 5:3724–3729
Yadav M, Xu Q (2013) Chem Commun 49:3327–3329
Zhao ZS, Zhang Y, Fang T, Han ZB, Liang FS (2020) ACS Appl Nano Mater 3:6316–6320
Zhang FY, Zhang JL, Zhang BX, Zheng LR, Cheng XY, Wan Q, Han BX, Zhang J (2020) Nat Commun 11:1431
Li JX, Li X, Tang H, Zhang YY, Han ZB (2019) Inorg Chem Commun 103:82–86
Tan P, Li GN, Fang RQ, Chen LY, Luque R, Li YW (2017) ACS Catal 7:2948–2955
Feng X, Hajek J, Jena HS, Wang G-B, Veerapandian SKP, Morent R, Geyter ND, Leyssens K, Hoffman AEJ, Meynen V, Marquez C, Vos DED, Speybroeck VV, Leus K, Voor PVD (2020) J Am Chem Soc 142:3174–3183
Dong XW, Yang Y, Che JX, Jun Z, Li XH, Gao L, Hu YZ, Liu XY (2018) Green Chem 20:4085–4093
Qi MH, Gao ML, Liu L, Han ZB (2018) Inorg Chem 57:14467–14470
Zhang YY, Li JX, Ding LL, Liu L, Wang SM, Han ZB (2018) Inorg Chem 57:13586–13593
Feng D, Gu ZY, Li JR, Jiang HL, Wei ZW, Zhou HC (2012) Angew Chem 51:10307–10310
Choi S, Oh M (2019) Angew Chem 58:866–871
Chen L, Wang HF, Li CX, Xu Q (2020) Chem Sci 11:5369–5403
Gu Y, Wu YN, Li L, Chen W, Li FT, Kitagawa S (2017) Angew Chem 56:15658–15662
Puthiaraj P, Yu K, Baeck SH, Ahn WS (2020) Catal Today 352:298–307
Gong YY, Yuan Y, Chen C, Zhang P, Wang JC, Serge Z, Somboon C, Francis V (2019) J Catal 371:106–115
Zhao MT, Deng K, He LC, Liu Y, Li GD, Zhao HJ, Tang ZY (2014) J Am Chem Soc 136:1738–1741
Gong YY, Yuan Y, Chen C, Zhang P, Wang JC, Anish K, Serge Z, Somboon C, Francis V (2019) J Catal 375:371–379
Satyabrata S, Sriram M, Suraj Prakash T, Ashutosh M, Priyabrat M, Dharitri R, Kulamani P (2019) Catal Sci Technol 9:6585–6597
Huang YB, Liu SJ, Lin ZJ, Li WJ, Li XF, Cao R (2012) J Catal 292:111–117
Wang QJ, Nobuko T, Mitsunori K, Xu Q (2018) ACS Catal 8:12041–12045
Bhadra BN, Vinu A, Serre C et al (2019) MOF-derived carbonaceous materials enriched with nitrogen: Preparation and applications in adsorption and catalysis. Mater Today 25:88–111
Chong SY, Wang TT, Cheng LC, Lv HY, Ji M (2019) Langmuir: ACS J Surf Colloids 35:495–503
Imteaz A, Tandra P, Nazmul Abedin K, Mithun S, Jong Sung Y, Sung Hwa J (2017) ACS Appl Mater Interfaces 9:10276–10285
Luis GT, Javier PC, Amirali Y, Jose HM, Pedro T, Inhar I, Felix Z, Daniel M (2019) Angew Chem 58:9512–9516
Cai MK, Li YL, Liu QL, Xue ZQ, Wang HP, Fan YN, Zhu KL, Ke ZF, Su CY, Li GQ (2019) Adv Sci (Weinh) 6:1802365
He HB, Li R, Yang ZH, Chai LY, Jin LF, Alhassan SI, Ren LL, Wang HY, Huang L (2021) Catal Today 375:10–29
Zhu QL, Xu Q (2014) Chem Soc Rev 43:5468–5512
Gong YY, Yuan Y, Chen C, Somboon C, Francis V (2020) J Catal 392:141–149
Ding D, Jiang Z, Jin JP, Li JJ, Ji D, Zhang YX, Zan L (2019) J Catal 375:21–31
Lee YR, Do XH, Hwang SS, Baek KY (2020) Catal Today 359:124–132
Li H, Pan Q, Ma Y, Guah X, Xue M, Fang Q, Yan Y, Valtchev V, Qiu S (2016) J Am Chem Soc 138:14783–14788
Zhang Y, Wang YX, Liu L, Wei N, Gao ML, Zhao D, Han Z-B (2018) Inorg Chem 57:2193–2198
Wang Z, Yuan X, Cheng Q, Zhang T, Luo J (2018) New J Chem 42:11610–11615
Acknowledgements
This work was financial supported by the National Natural Science Foundation of China (Grant No 21671090), Scientific Research Fund of Liaoning Provincial Education Department (Grant No LJKZ0098) and Project supported by Liaoning Provincial Natural Science Foundation of China (Grant No 2021-MS-239).
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MY: Writing—Original Draft, Software, Investigation, Project administration, Formal analysis, Funding acquisition. YSB: Investigation, Validation. MLZ: Visualization, Software. SW: Participate in some characterization works. YHC, WL, LCL and LXM: Resources, Visualization, Data curation. Zheng-Bo Han: Writing—Review & Editing. YYZ: Conceptualization, Methodology, Resources, Writing-Review & Editing, Supervision.
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Yang, M., Bao, YS., Zhou, ML. et al. An Efficient Bifunctional Core–Shell MIL-101(Cr)@MOF-867 Composite to Catalyze Deacetalization–Knoevenagel Tandem Reaction. Catal Lett 153, 3561–3568 (2023). https://doi.org/10.1007/s10562-022-04259-x
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DOI: https://doi.org/10.1007/s10562-022-04259-x