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Issue 20, 2017
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5,5′-Bistriazoles as axially chiral, multidentate ligands: synthesis, configurational stability and catalytic application of their scandium(III) complexes

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Abstract

The design and development of 5,5′-bistriazoles featuring aminomethyl substituents is discussed. An efficient synthetic procedure for the selective preparation of 4,4′-bis(aminomethyl)-5,5′-bistriazoles from commercially available propargylamine derivatives and benzyl azide has been optimized. The first experimental determination of the configurational stability of 5,5′-bistriazoles is disclosed on the basis of rotational energy barriers and half-life times. Fast racemization was observed for a bistriazole possessing solely axial chirality whereas a more heavily substituted bistriazole involving axial and central chirality proved to be configurationally stable. A successful catalytic application has been implemented by using a N,N-dimethylpropargylamine-derived 5,5′-bistriazole as a multidentate ligand controlling the product selectivity (single vs. double addition) in scandium(III)-catalyzed nucleophilic additions of indoles to isatin electrophiles.

Graphical abstract: 5,5′-Bistriazoles as axially chiral, multidentate ligands: synthesis, configurational stability and catalytic application of their scandium(iii) complexes

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Publication details

The article was received on 26 Jul 2017, accepted on 24 Sep 2017 and first published on 28 Sep 2017


Article type: Paper
DOI: 10.1039/C7CY01518F
Citation: Catal. Sci. Technol., 2017,7, 4830-4841
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    5,5′-Bistriazoles as axially chiral, multidentate ligands: synthesis, configurational stability and catalytic application of their scandium(III) complexes

    P. Etayo, E. C. Escudero-Adán and M. A. Pericàs, Catal. Sci. Technol., 2017, 7, 4830
    DOI: 10.1039/C7CY01518F

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