Synthesis and catalytic applications of 1,2,3-triazolylidene gold( i ) complexes in silver-free oxazoline syntheses and C–H bond activation

Pretorius, René; Fructos, Manuel R.; Müller-Bunz, Helge; Gossage, Robert A.; Pérez, Pedro J.; Albrecht, Martin (2016). Synthesis and catalytic applications of 1,2,3-triazolylidene gold( i ) complexes in silver-free oxazoline syntheses and C–H bond activation. Dalton transactions, 45(37), pp. 14591-14602. Royal Society of Chemistry 10.1039/C6DT02181F

[img]
Preview
Text
c6dt02181f.pdf - Published Version
Available under License Creative Commons: Attribution (CC-BY).

Download (994kB) | Preview

A series of novel 1,2,3-triazolylidene gold(I) chloride complexes have been synthesised and fully characterised. Silver-free methodologies for chloride ion abstraction of these complexes were evaluated for their potential as Au-based catalyst precursors. Using simple potassium salts or MeOTf as chloride scavengers produced metal complexes that catalyse both the regioselective synthesis of oxazolines and the C–H activation of benzene or styrene for carbene transfer from ethyl diazoacetate. These results indicate that Ag-free activation of 1,2,3-triazolylidene gold(I) chloride complexes is feasible for the generation of catalytically active Au triazolylidene species. However, silver-mediated activation imparts substantially higher catalytic activity in oxazoline synthesis.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Pretorius, René and Albrecht, Martin

Subjects:

500 Science > 540 Chemistry

ISSN:

1477-9226

Publisher:

Royal Society of Chemistry

Funders:

[18] European Research Council
[152] European Cooperation in Science and Technology

Projects:

[1134] Exploiting Synergistic Properties of Mesoionic Carbene Complexes: Teaching Rusty Metals Challenging Catalysis
[1133] Catalytic Routines for Small Molecule Activation

Language:

English

Submitter:

Eik Szee Goh Aschauer

Date Deposited:

19 Jan 2017 16:16

Last Modified:

26 Mar 2019 14:24

Publisher DOI:

10.1039/C6DT02181F

BORIS DOI:

10.7892/boris.93944

URI:

https://boris.unibe.ch/id/eprint/93944

Actions (login required)

Edit item Edit item
Provide Feedback