Abstract
The design and construction of organocatalysts that combined the homogeneous and heterogeneous natures to realize efficient catalysis are highly desired and challenging. Functionalized-polymers, a kind of flexible materials, provide a platform to modulate the states of immobilized catalysts in rigid supports. Herein, a chiral polymer (CP) mediated catalyst containing Pd NPs have been reported (CP@Pd@MOF-808). Chiral active sites were anchored on the polymer, and the chiral polymer threaded within the host pores of MOFs to promise the homogeneousness of chiral sites in a heterogeneous support MOF-808. This strategy kept the flexibility and freedom of chiral sites after immobilization, thus exhibited comparable performances with the corresponding homogeneous catalyst. The well-designed CP@Pd@MOF-808 was applied to sequential asymmetric reactions with excellent reactivity and stereoselectivity (up to 89% yields and 95% ee values), which were even better than that of homogeneous catalyst.
Graphical Abstract
A rationally designed Chiral Polymer-Mediated MOF catalyst containing metal NPs was developed for sequential reaction with high efficiency.
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References
MacMillan DWC (2008) Nature 455:304–308
Tang Z, Jiang F, Yu L, Cui X, Gong L, Mi A, Jiang Y, Wu Y (2003) J Am Chem Soc 125:5262–5263
Ni H, Chan W, Lu Y (2018) Chem Rev 118:9344–9411
Wang H, Zhou ZX, Kurmoo M, Liu YJ, Zeng MH (2019) Org Lett 21:2847–2850
Zhang NJ, Ma WT, Li JW, Liu YJ, Zeng MH (2021) Asian J Org Chem 10:1113–1116
Wu C, Zhao M (2017) Adv Mater 29:1605446
Hu C, Bai Y, Hou M, Wang Y, Wang L, Cao X, Chan CW, Sun H, Li W, Ge J, Ren K (2020) Sci Adv 6:x5785
Li YM, Yuan J, Ren H, Ji CY, Tao Y, Wu Y, Chou LY, Zhang YB, Cheng L (2021) J Am Chem Soc 143:15378–15390
Sun Q, Fu C, Aguila B, Perman J, Wang S, Huang H, Xiao F, Ma S (2018) J Am Chem Soc 140:984–992
Liang J, Gao S, Liu J, Zulkifli MYB, Xu J, Scott J, Chen V, Shi J, Rawal A, Liang K (2021) Angew Chem Int Ed 60:5421–5428
Chen Y, Jiménez-Ángeles F, Qiao B, Krzyaniak MD, Sha F, Kato S, Gong X, Buru CT, Chen Z, Zhang X, Gianneschi NC, Wasielewski MR, de La Cruz MO, Farha OK (2020) J Am Chem Soc 142:18576–18582
Wu Y, Chen C, Yan X, Sun X, Zhu Q, Li P, Li Y, Liu S, Ma J, Huang Y, Han B (2021) Angew Chem Int Ed 60:20803–20810
Wei T, Wu S, Huang Y, Lo W, Williams BP, Chen S, Yang H, Hsu Y, Lin Z, Chen X, Kuo P, Chou L, Tsung C, Shieh F (2019) Nat Commun 10:5002
Yin Z, Wan S, Yang J, Kurmoo M, Zeng MH (2019) Coordin Chem Rev 378:500–512
Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM (2013) Science 341:1230444
Kirchon A, Feng L, Drake HF, Joseph EA, Zhou HC (2018) Chem Soc Rev 47:8611–8638
Yuan S, Feng L, Wang K, Pang J, Bosch M, Lollar C, Sun Y, Qin J, Yang X, Zhang P, Wang Q, Zou L, Zhang Y, Zhang L, Fang Y, Li J, Zhou HC (2018) Adv Mater 30:1704303
Wei Y, Zhang M, Liao P, Lin R, Li T, Shao G, Zhang JP, Chen XM (2015) Nat Commun 6:8348
Baek J, Rungtaweevoranit B, Pei X, Park M, Fakra SC, Liu Y, Matheu R, Alshmimri SA, Alshehri S, Trickett CA, Somorjai GA, Yaghi OM (2018) J Am Chem Soc 140:18208–18216
Lan G, Li Z, Veroneau SS, Zhu Y, Xu Z, Wang C, Lin W (2018) J Am Chem Soc 140:12369–12373
Liu Y, Xuan W, Cui Y (2010) Adv Mater 22:4112–4135
Shieh F, Wang S, Yen C, Wu C, Dutta S, Chou L, Morabito JV, Hu P, Hsu M, Wu KCW, Tsung C (2015) J Am Chem Soc 137:4276–4279
Hossain S, Jin M, Park J, Yingjie Q, Yang D (2013) Catal Lett 143:122–125
Drake T, Ji P, Lin W (2018) Accounts Chem Res 51:2129–2138
Comito RJ, Wu Z, Zhang G, Lawrence JA, Korzyński MD, Kehl JA, Miller JT, Dincă M (2018) Angew Chem Int Ed 57:8135–8139
Wang C, Wang J, Lin W (2012) J Am Chem Soc 134:19895–19908
Roberts JM, Fini BM, Sarjeant AA, Farha OK, Hupp JT, Scheidt KA (2012) J Am Chem Soc 134:3334–3337
Li M, Qiao S, Zheng Y, Andaloussi YH, Li X, Zhang Z, Li A, Cheng P, Ma S, Chen Y (2020) J Am Chem Soc 142:6675–6681
Chen Y, Zhou Y, Wang H, Lu J, Uchida T, Xu Q, Yu S, Jiang H (2015) ACS Catal 5:2062–2069
Agami C, Puchot C, Sevestre H (1986) Tetrahedron Lett 27:1501–1504
Zhu C, Xia Q, Chen X, Liu Y, Du X, Cui Y (2016) ACS Catal 6:7590–7596
Fan Y, You E, Xu Z, Lin W (2021) J Am Chem Soc 143:18871–18876
Dong X, Yang Y, Che J, Zuo J, Li X, Gao L, Hu Y, Liu X (2018) Green Chem 20:4085–4093
Wu X, Han X, Zhang J, Jiang H, Hou B, Liu Y, Cui Y (2019) Organometallics 38:3474–3479
Gao L, Li CV, Chan K, Chen Z (2014) J Am Chem Soc 136:7209–7212
Lee DT, Zhao J, Oldham CJ, Peterson GW, Parsons GN (2017) ACS Appl Mater Inter 9:44847–44855
Yi B, Wong YL, Hou C, Zhang J, Xu Z, Yao X (2021) Adv Mater Interfaces 8:2001202
Yang S, Karve VV, Justin A, Kochetygov I, Espín J, Asgari M, Trukhina O, Sun DT, Peng L, Queen WL (2021) Coordin Chem Rev 427:213525
Calvez CL, Zouboulaki M, Petit C, Peeva L, Shirshova N (2016) RSC Adv 6:17314–17317
Sachdeva S, Soccol D, Gravesteijn DJ, Kapteijn F, Sudhölter EJR, Gascon J, de Smet LCPM (2016) ACS Sensors 1:1188–1192
Nagata S, Kokado K, Sada K (2015) Chem Commun 51:8614–8617
Cheng L, Cao LM, Ren H, Guo QQ, Deng HF, Li YM (2021). Catal Lett. https://doi.org/10.1007/s10562-021-03719-0
Cheng L, Zhao KY, Zhang QS, Li YM, Zhai QC, Chen JX, Lou YB (2020) Inorg Chem 59:7991–8001
Liang W, Chevreau H, Ragon F, Southon PD, Peterson VK, D’Alessandro DM (2014) CrystEngComm 16:6530–6533
Trickett CA, Osborn Popp TM, Su J, Yan C, Weisberg J, Huq A, Urban P, Jiang J, Kalmutzki MJ, Liu Q, Baek J, Head-Gordon MP, Somorja GAI, Reimer JA, Yaghi OM (2019) Nat Chem 11:170–176
Moon S, Liu Y, Hupp JT, Farha OK (2015) Angew Chem Int Ed 54:6795–6799
Salama RS, Mannaa MA, Altass HM, Ibrahim AA, Khder AES (2021) RSC Adv 11:4318–4326
Wang J, Li T, Zhao Z, Zhang X, Pang W (2021). Catal Lett. https://doi.org/10.1007/s10562-021-03731-4
Karve VV, Sun DT, Trukhina O, Yang S, Oveisi E, Luterbacher J, Queen WL (2020) Green Chem 22:368–378
Zhu J, Xu D, Ding LJ, Wang PC (2021) Chem Eur J 27:2707–2716
Farrag M (2021) Mesopor Micropor Mat 312:110783
Cheng L, Wang J, Qi Q, Zhang X, Yu H, Gou S, Fang L (2014) CrystEngComm 16:10056–10065
Cui M, Wang A, Liu Y, Xiao H, Li F, Zhou L, Fang S, Li X (2020) RSC Adv 10:39359–39365
Liu L, Zhou X, Guo L, Yan S, Li Y, Jiang S, Tai X (2020) RSC Adv 10:33417–33427
Lirio S, Shih YH, So PB, Liu LH, Yen YT, Furukawa S, Liu WL, Huang HY, Lin CH (2021) Dalton Trans 50:1866–1873
Yang JW, Chandler C, Stadler M, Kampen D, List B (2008) Nature 452:453–455
Hu Y, Liu C, Wang J, Ren X, Kan X, Dong Y (2019) Inorg Chem 58:4722–4730
Wu X, Han X, Zhang J, Jiang H, Hou B, Liu Y, Cui Y (2019) Organometallic 38:3474–3479
Thür R, Van Velthoven N, Lemmens V, Bastin M, Smolders S, De Vos D, Vankelecom IFJ (2019) ACS Appl Mater Inter 11:44792–44801
Xu J, Liu J, Li Z, Wang X, Wang Z (2019) J Mater Sci 54:12911–12924
Acknowledgements
We are grateful for financial support from the Natural Science Foundation of Jiangsu Province (BK20131289), the Fundamental Research Funds for the Central Universities, the National Natural Science Foundation of China (No. 21471031) and the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
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Li, YM., Cao, L., Ren, H. et al. Chiral Polymer-Mediated Pd@MOF-808 for Efficient Sequential Asymmetric Reaction. Catal Lett 153, 1193–1204 (2023). https://doi.org/10.1007/s10562-022-04053-9
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DOI: https://doi.org/10.1007/s10562-022-04053-9