Issue 20, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Jul 2017
Accepted
24 Sep 2017
First published
28 Sep 2017

Catal. Sci. Technol., 2017,7, 4830-4841

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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