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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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
27 August 2012
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| In: |
Journal of organometallic chemistry
Year: 2012, Volume: 719, Pages: 54-63 |
| ISSN: | 1872-8561 |
| DOI: | 10.1016/j.jorganchem.2012.08.018 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1016/j.jorganchem.2012.08.018 Verlag, Volltext: https://www.sciencedirect.com/science/article/pii/S0022328X12005141 
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| Author Notes: | Stefanie C. Holm, Frank Rominger, Bernd F. Straub |
| Summary: | 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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| Item Description: | Gesehen am 23.08.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1872-8561 |
| DOI: | 10.1016/j.jorganchem.2012.08.018 |