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Thiol-functionalized 1,2,4-triazolium salt as carbene ligand precursor

Abstract: A thiol-functionalized 1,2,4-triazolylidene ligand precursor salt was synthesized from 2-(4-methoxybenzylthio)aniline. Removal of the protecting group under strongly acidic conditions (trifluoroacetic acid/trifluoromethanesulfonic acid) yielded a 1,2,4-triazolium salt comprising a free thi...

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Bibliographische Detailangaben
Hauptverfasser: Seitz, Stefanie Christine (VerfasserIn) , Rominger, Frank (VerfasserIn) , Straub, Bernd Franz (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 27 August 2012
In: Journal of organometallic chemistry
Year: 2012, Jahrgang: 719, Pages: 54-63
ISSN:1872-8561
DOI:10.1016/j.jorganchem.2012.08.018
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1016/j.jorganchem.2012.08.018
Verlag, Volltext: https://www.sciencedirect.com/science/article/pii/S0022328X12005141
Volltext
Verfasserangaben:Stefanie C. Holm, Frank Rominger, Bernd F. Straub

MARC

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520 |a Abstract: A thiol-functionalized 1,2,4-triazolylidene ligand precursor salt was synthesized from 2-(4-methoxybenzylthio)aniline. Removal of the protecting group under strongly acidic conditions (trifluoroacetic acid/trifluoromethanesulfonic acid) yielded a 1,2,4-triazolium salt comprising a free thiophenol moiety as was confirmed by X-ray analysis. The fairly air-stable thiophenol was oxidized by DMSO resulting in ring closure to a benzothiazole. Deprotonation and metalation resulted in the cis- and trans-isomers of the square-planar bis(NHC-thiolato) Ni(II), Pd(II) and Pt(II) complexes. The palladium complex was successfully employed as catalyst in C–C, C–N and C–S cross-coupling reactions. Chlorobenzene was activated only in the amination reaction. Cobalt dichloride formed an octahedral Co(III) complex under oxidation of the metal center. A η3−allyldicarbonylmolybdenum(II) complex of the C,S-ligand was prepared. 
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