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. 2022 Jun 1;20(21):4314-4319.
doi: 10.1039/d2ob00439a.

Chirality-driven self-assembly: application toward renewable/exchangeable resin-immobilized catalysts

Elizabeth M Menuey  1 , John Zhou  1 , Shuyuan Tian  1 , Reid E Brenner  1 , Zhaoyang Ren  2 , Duy H Hua  2 , Kathleen V Kilway  1 , Shin A Moteki  1
Affiliations

Chirality-driven self-assembly: application toward renewable/exchangeable resin-immobilized catalysts

Elizabeth M Menuey et al. Org Biomol Chem. .

Abstract

Resin-immobilized catalysts were prepared through chirality-driven self-assembly. The method allows the resin-immobilized catalyst to be regenerated under mild conditions and in situ catalyst exchange to be carried out quantitatively. The uniqueness of the methodology was demonstrated by the preparation of a catalyst for TEMPO oxidation as well as a two-step sequential TEMPO oxidation/aldol condensation sequence enabled by facile catalyst exchange.

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Conflict of interest statement

Conflicts of interest

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1
Non-selective (A and B) versus selective self-assembly (C and D).
Scheme 2
Scheme 2
Renewability and exchangeability of the self-assembly based resin immobilized catalysts.
Scheme 3
Scheme 3
One-pot preparation of fmoc-derived resin used for quantifying the functional capacity.
Scheme 4
Scheme 4
Renewability and exchangeability of the self-assembly based resin immobilized catalysts.
Scheme 5
Scheme 5
A one-pot preparation of resin immobilized TEMPO catalyst (RR,RR)-11.
Scheme 6
Scheme 6
Sequential oxidation/aldol reaction using catalyst exchangeable resin.
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References

    1. Miceli M, Frontera P, Macario A and Malara A, Catalysts, 2021, 11, 591–607;
    2. Susam ZD and Tanyeli C, Asian J. Org. Chem, 2021, 10, 1251–1266;
    3. Liu M, Wu J and Hou H, Chem. – Eur. J, 2019, 25, 2935–2948; - PubMed
    4. Ye R, Zhukhovitskiy AV, Deraedt CV, Toste FD and Somorjai GA, Acc. Chem. Res, 2017, 50, 1894–1901; - PubMed
    5. Moberg C, Acc. Chem. Res, 2016, 49, 2736–2745. - PubMed
    1. Molnar A and Papp A, Coord. Chem. Rev, 2017, 349, 1–65;
    2. Sheldon RA, Chem. Soc. Rev, 2012, 41, 1437–1451; - PubMed
    3. Anastas PT and Eghbali N, Chem. Soc. Rev, 2010, 39, 301–312. - PubMed
    1. Zhang H, Li H, Xu CC and Yang S, ACS Catal., 2019, 9, 10990–11029;
    2. Munnik P, de Jongh PE and de Jong KP, Chem. Rev, 2015, 115, 6687–6718; - PubMed
    3. Barak-Kulbak E, Goren K and Portnoy M, Pure Appl. Chem, 2014, 86, 1805–1818;
    4. Benaglia M, Puglisi A and Cozzi F, Chem. Rev, 2003, 103, 3401–3429. - PubMed
    1. Trindade AF, Gois PMP and Afonso CAM, Chem. Rev, 2009, 109, 418–514; - PubMed
    2. Lu J and Toy PH, Chem. Rev, 2009, 109, 815–838; - PubMed
    3. Heitbaum M, Glorius F and Escher I, Angew. Chem., Int. Ed, 2006, 45, 4732–4762; - PubMed
    4. Cozzi F, Adv. Synth. Catal, 2006, 348, 1367–1390;
    5. Benaglia M, New J. Chem, 2006, 30, 1525–1533.
    1. Lebreton L, Egger M and Slat B, Sci. Rep, 2019, 9, 1–10; - PMC - PubMed
    2. Sheldon RA and Woodley JM, Chem. Rev, 2018, 118, 801–838; - PubMed
    3. Jambeck JR, Geyer R, Wilcox C, Siegler TR, Perryman M, Andrady A, Narayan R and Law KL, Science, 2015, 347, 768–771. - PubMed

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