Balancing Bulkiness in Gold(I) Phosphino-triazole Catalysis.

Balancing Bulkiness in Gold(I) Phosphino-triazole Catalysis.

Zhao, Yiming;Wakeling, Matthew G;Meloni, Fernanda;Sum, Tze Jing;van Nguyen, Huy;Buckley, Benjamin R;Davies, Paul W;Fossey, John S;
european journal of organic chemistry 2019 Vol. 2019 pp. 5540-5548
321
zhao2019balancingeuropean

Abstract

The syntheses of a series of 1-phenyl-5-phosphino 1,2,3-triazoles are disclosed, within which, the phosphorus atom (at the 5-position of a triazole) is appended by one, two or three triazole motifs, and the valency of the phosphorus(III) atom is completed by two, one or zero ancillary (phenyl or cyclohexyl) groups respectively. This series of phosphines was compared with tricyclohexylphosphine and triphenylphosphine to study the effect of increasing the number of triazoles appended to the central phosphorus atom from zero to three triazoles. Gold(I) chloride complexes of the synthesised ligands were prepared and analysed by techniques including single-crystal X-ray diffraction structure determination. Gold(I) complexes were also prepared from 1-(2,6-dimethoxy)-phenyl-5-dicyclohexyl-phosphino 1,2,3-triazole and 1-(2,6-dimethoxy)-phenyl-5-diphenyl-phosphino 1,2,3-triazole ligands. The crystal structures thus obtained were examined using the web tool and percentage buried volumes determined. The effectiveness of these gold(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed. Furthermore, the regioselectivity of hydration of but-1-yne-1,4-diyldibenzene was probed.

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61228
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10.1002/ejoc.201900850
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