Balancing bulkiness in gold(I) phosphino-triazole catalysis

Research output: Contribution to journalArticlepeer-review

Standard

Balancing bulkiness in gold(I) phosphino-triazole catalysis. / Zhao, Yiming; Wakeling, Mat; Meloni, Fernanda; Sum, TJ; Nguyen, Van Huy; Buckley, Benjamin R; Davies, Paul; Fossey, John.

In: European Journal of Organic Chemistry, Vol. 2019, No. 31-32, 01.09.2019, p. 5540-5548.

Research output: Contribution to journalArticlepeer-review

Harvard

APA

Vancouver

Author

Zhao, Yiming ; Wakeling, Mat ; Meloni, Fernanda ; Sum, TJ ; Nguyen, Van Huy ; Buckley, Benjamin R ; Davies, Paul ; Fossey, John. / Balancing bulkiness in gold(I) phosphino-triazole catalysis. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 31-32. pp. 5540-5548.

Bibtex

@article{beae30f0cb4640c4927062073ff4d8f6,
title = "Balancing bulkiness in gold(I) phosphino-triazole catalysis",
abstract = "The syntheses of a series of 1-phenyl-5-phosphino1,2,3-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-phos-phino 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 SambVca (2.0)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.",
keywords = "Click chemistry, Gold, Homogeneous catalysis, Phosphane ligands, Triazoles",
author = "Yiming Zhao and Mat Wakeling and Fernanda Meloni and TJ Sum and Nguyen, {Van Huy} and Buckley, {Benjamin R} and Paul Davies and John Fossey",
year = "2019",
month = sep,
day = "1",
doi = "10.1002/ejoc.201900850",
language = "English",
volume = "2019",
pages = "5540--5548",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "31-32",

}

RIS

TY - JOUR

T1 - Balancing bulkiness in gold(I) phosphino-triazole catalysis

AU - Zhao, Yiming

AU - Wakeling, Mat

AU - Meloni, Fernanda

AU - Sum, TJ

AU - Nguyen, Van Huy

AU - Buckley, Benjamin R

AU - Davies, Paul

AU - Fossey, John

PY - 2019/9/1

Y1 - 2019/9/1

N2 - The syntheses of a series of 1-phenyl-5-phosphino1,2,3-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-phos-phino 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 SambVca (2.0)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.

AB - The syntheses of a series of 1-phenyl-5-phosphino1,2,3-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-phos-phino 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 SambVca (2.0)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.

KW - Click chemistry

KW - Gold

KW - Homogeneous catalysis

KW - Phosphane ligands

KW - Triazoles

UR - http://www.scopus.com/inward/record.url?scp=85070063894&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201900850

DO - 10.1002/ejoc.201900850

M3 - Article

C2 - 31598094

VL - 2019

SP - 5540

EP - 5548

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 31-32

ER -