Use this identifier to quote or link this document: http://hdl.handle.net/2072/450554

Title:	5,5’-Bistriazoles as axially chiral, multidentate ligands: Synthesis, configurational stability and catalytic application of their scandium(III) complexes
Author:	Etayo, Pablo; Escudero-Adán, Eduardo C.; Pericàs, Miquel A.
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.
Publication date:	2017-09-28
Subject(s):	54
Rights:	L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/
Pages:	4830 p.
Document type:	Article Article - Accepted version
DOI:	doi.org/10.1039/C7CY01518F
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