Metal-mediated C–C bond formation in a platinum(II)-coordinated dipyridylmethane ligand: an unusual example of “ipso-coupling” with solvent involvement

We report the chelation-assisted oxidative CH extrusion from a Pt -coordinated dipyridylmethane, resulting in the formation of a 2,2′-bipyridyl ligand. This unusual one-pot reaction (solvent: dimethylformamide, DMF), which is quantitative, proceeds in air at mildly elevated temperature, with CH → C=...

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Published inZeitschrift für Naturforschung. B, A journal of chemical sciences Vol. 77; no. 6; pp. 419 - 423
Main Authors Sommerfeld, Nadine S., Gülzow, Jana, Kohl, Julia, Grohmann, Andreas
Format Journal Article
LanguageEnglish
Published De Gruyter 27.06.2022
Subjects
cross coupling
C–C bond forming reaction
fragment coupling
functional group extrusion
platinum(II)
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Summary:We report the chelation-assisted oxidative CH extrusion from a Pt -coordinated dipyridylmethane, resulting in the formation of a 2,2′-bipyridyl ligand. This unusual one-pot reaction (solvent: dimethylformamide, DMF), which is quantitative, proceeds in air at mildly elevated temperature, with CH → C=O conversion, decarbonylation, and C–C coupling of the two pyridyl residues (“fragment coupling”). It constitutes, in effect, a chelate ring contraction by one member.
ISSN:0932-0776
1865-7117
DOI:10.1515/znb-2022-0043