Dynamic Covalent Organocatalysts Discovered from Catalytic Systems through Rapid Deconvolution Screening
2015 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 36, 12735-12740 p.Article in journal (Refereed) Published
The first example of a bifunctional organocatalyst assembled through dynamic covalent chemistry (DCC) is described. The catalyst is based on reversible imine chemistry and can catalyze the Morita-Baylis-Hillman (MBH) reaction of enones with aldehydes or N-tosyl imines. Furthermore, these dynamic catalysts were shown to be optimizable through a systemic screening approach, in which large mixtures of catalyst structures were generated, and the optimal catalyst could be directly identified by using dynamic deconvolution. This strategy allowed one-pot synthesis and in situ evaluation of several potential catalysts without the need to separate, characterize, and purify each individual structure. The systems were furthermore shown to catalyze and re-equilibrate their own formation through a previously unknown thiourea-catalyzed transimination process.
Place, publisher, year, edition, pages
2015. Vol. 21, no 36, 12735-12740 p.
catalyst screening, dynamic covalent chemistry, organocatalysis, Schiff bases, transimination
IdentifiersURN: urn:nbn:se:kth:diva-173763DOI: 10.1002/chem.201502088ISI: 000360312100026PubMedID: 26174068ScopusID: 2-s2.0-84940178757OAI: oai:DiVA.org:kth-173763DiVA: diva2:855914
FunderSwedish Research Council
QC 201509222015-09-222015-09-182015-09-22Bibliographically approved