Intramolecular hydroamination catalysed by Ag complexes stabilised in situ by bidentate ligands

Sophie R. Beeren; Serin L. Dabb; Barbara A. Messerle

doi:10.1016/j.jorganchem.2008.10.038

Intramolecular hydroamination catalysed by Ag complexes stabilised in situ by bidentate ligands

Sophie R. Beeren, Serin L. Dabb, Barbara A. Messerle

University of New South Wales

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A series of silver complexes generated in situ from AgOSO2CF3 (AgOTf) and a range of bidentate ligands were investigated as catalysts for the intramolecular hydroamination of 4-pentyn-1-amine. A variety of P- and N-donor ligands were tested including the novel pyrazole-phosphine ligand 1-(2-(diphenylphosphino)phenyl)pyrazole. The best catalyst was formed from equimolar amounts of the P,N-donor ligand 1-(2-(diphenylphosphino)ethyl)pyrazole and AgOTf, which achieved a turnover rate of 129 h-1 for the cyclisation of 4-pentyn-1-amine.

Original language	English
Journal	Journal of Organometallic Chemistry
Volume	694
Issue number	2
Pages (from-to)	309-312
Number of pages	4
ISSN	0022-328X
DOIs	https://doi.org/10.1016/j.jorganchem.2008.10.038
Publication status	Published - 2009
Externally published	Yes

Keywords

Biochemistry
Inorganic Chemistry
Organic Chemistry
Physical and Theoretical Chemistry
Materials Chemistry
Alkynylamine
Bidentate ligand
Cyclisation
Hydroamination
Silver catalyst
Triflate
Amination
Amines
Catalysis
Catalysts
Cyclization
Organic compounds
Phosphorus compounds
Silver
Sugar (sucrose)
Ligands

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10.1016/j.jorganchem.2008.10.038

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title = "Intramolecular hydroamination catalysed by Ag complexes stabilised in situ by bidentate ligands",

abstract = "A series of silver complexes generated in situ from AgOSO2CF3 (AgOTf) and a range of bidentate ligands were investigated as catalysts for the intramolecular hydroamination of 4-pentyn-1-amine. A variety of P- and N-donor ligands were tested including the novel pyrazole-phosphine ligand 1-(2-(diphenylphosphino)phenyl)pyrazole. The best catalyst was formed from equimolar amounts of the P,N-donor ligand 1-(2-(diphenylphosphino)ethyl)pyrazole and AgOTf, which achieved a turnover rate of 129 h-1 for the cyclisation of 4-pentyn-1-amine. ",

keywords = "Biochemistry, Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Materials Chemistry, Alkynylamine, Bidentate ligand, Cyclisation, Hydroamination, Silver catalyst, Triflate, Amination, Amines, Catalysis, Catalysts, Cyclization, Organic compounds, Phosphorus compounds, Silver, Sugar (sucrose), Ligands",

author = "Beeren, {Sophie R.} and Dabb, {Serin L.} and Messerle, {Barbara A.}",

year = "2009",

doi = "10.1016/j.jorganchem.2008.10.038",

language = "English",

volume = "694",

pages = "309--312",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "2",

}

TY - JOUR

T1 - Intramolecular hydroamination catalysed by Ag complexes stabilised in situ by bidentate ligands

AU - Beeren, Sophie R.

AU - Dabb, Serin L.

AU - Messerle, Barbara A.

PY - 2009

Y1 - 2009

N2 - A series of silver complexes generated in situ from AgOSO2CF3 (AgOTf) and a range of bidentate ligands were investigated as catalysts for the intramolecular hydroamination of 4-pentyn-1-amine. A variety of P- and N-donor ligands were tested including the novel pyrazole-phosphine ligand 1-(2-(diphenylphosphino)phenyl)pyrazole. The best catalyst was formed from equimolar amounts of the P,N-donor ligand 1-(2-(diphenylphosphino)ethyl)pyrazole and AgOTf, which achieved a turnover rate of 129 h-1 for the cyclisation of 4-pentyn-1-amine.

AB - A series of silver complexes generated in situ from AgOSO2CF3 (AgOTf) and a range of bidentate ligands were investigated as catalysts for the intramolecular hydroamination of 4-pentyn-1-amine. A variety of P- and N-donor ligands were tested including the novel pyrazole-phosphine ligand 1-(2-(diphenylphosphino)phenyl)pyrazole. The best catalyst was formed from equimolar amounts of the P,N-donor ligand 1-(2-(diphenylphosphino)ethyl)pyrazole and AgOTf, which achieved a turnover rate of 129 h-1 for the cyclisation of 4-pentyn-1-amine.

KW - Biochemistry

KW - Inorganic Chemistry

KW - Organic Chemistry

KW - Physical and Theoretical Chemistry

KW - Materials Chemistry

KW - Alkynylamine

KW - Bidentate ligand

KW - Cyclisation

KW - Hydroamination

KW - Silver catalyst

KW - Triflate

KW - Amination

KW - Amines

KW - Catalysis

KW - Catalysts

KW - Cyclization

KW - Organic compounds

KW - Phosphorus compounds

KW - Silver

KW - Sugar (sucrose)

KW - Ligands

U2 - 10.1016/j.jorganchem.2008.10.038

DO - 10.1016/j.jorganchem.2008.10.038

M3 - Journal article

VL - 694

SP - 309

EP - 312

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 2

ER -

Intramolecular hydroamination catalysed by Ag complexes stabilised in situ by bidentate ligands

Abstract

Keywords

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