Scalable and Recyclable All-Organic Colloidal Cascade Catalysts.
cascade reactions
catalysis
compartmentalization
emulsion polymerization
microreactors
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 Jan 2021
04 Jan 2021
Historique:
received:
07
06
2020
pubmed:
22
9
2020
medline:
22
9
2020
entrez:
21
9
2020
Statut:
ppublish
Résumé
We report on the synthesis of core-shell microparticles (CSMs) with an acid catalyst in the core and a base catalyst in the shell by surfactant-free emulsion polymerization (SFEP). The organocatalytic monomers were separately copolymerized in three synthetic steps allowing the spatial separation of incompatible acid and base catalysts within the CSMs. Importantly, a protected and thermo-decomposable sulfonate monomer was used as acid source to circumvent the neutralization of the base catalyst during shell formation, which was key to obtain stable, catalytically active CSMs. The catalysts showed excellent performance in an established one-pot model cascade reaction in various solvents (including water), which involved an acid-catalyzed deacetalization followed by a base-catalyzed Knoevenagel condensation. The CSMs are easily recycled, modified, and their synthesis is scalable, making them promising candidates for organocatalytic applications.
Identifiants
pubmed: 32954613
doi: 10.1002/anie.202008104
pmc: PMC7821152
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
237-241Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : GR 5075/2-1
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
Références
Chem Commun (Camb). 2013 Sep 14;49(71):7821-3
pubmed: 23892495
Curr Opin Biotechnol. 2014 Aug;28:10-6
pubmed: 24832069
J Am Chem Soc. 2015 Jan 28;137(3):1362-71
pubmed: 25603470
Chem Commun (Camb). 2014 Dec 7;50(94):14778-81
pubmed: 25317577
Angew Chem Int Ed Engl. 2021 Jan 4;60(1):237-241
pubmed: 32954613
Chemistry. 2011 Apr 11;17(16):4552-60
pubmed: 21365697
J Am Chem Soc. 2008 May 21;130(20):6322-3
pubmed: 18433122
Macromol Rapid Commun. 2019 Jan;40(1):e1800580
pubmed: 30368964
Nat Chem. 2010 Mar;2(3):167-78
pubmed: 21124474
Nat Chem. 2015 Jun;7(6):477-82
pubmed: 25991525
Nat Chem. 2013 Feb;5(2):93-9
pubmed: 23344429
Chem Soc Rev. 2006 Nov;35(11):1068-83
pubmed: 17057836
Angew Chem Int Ed Engl. 2012 Sep 3;51(36):9164-8
pubmed: 22865743
Angew Chem Int Ed Engl. 2005 Oct 7;44(39):6384-7
pubmed: 16161169
Chemistry. 2016 Apr 18;22(17):5914-8
pubmed: 26970553
Chem Sci. 2016 Aug 1;7(8):5568-5572
pubmed: 30034697
Chemistry. 2018 Dec 12;24(70):18648-18652
pubmed: 30276903
Chem Soc Rev. 2017 Jan 3;46(1):126-157
pubmed: 27841411
Angew Chem Int Ed Engl. 2010;49(1):184-7
pubmed: 19957253
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):146-50
pubmed: 24254810
Chem Rev. 2016 Feb 10;116(3):1053-93
pubmed: 26322859
J Am Chem Soc. 2015 Oct 14;137(40):12984-9
pubmed: 26426145
Angew Chem Int Ed Engl. 2011 Oct 4;50(41):9615-9
pubmed: 21919160
Nat Commun. 2017 Sep 22;8(1):663
pubmed: 28939810
J Am Chem Soc. 2019 Apr 3;141(13):5220-5230
pubmed: 30776224