Abstract
2-(3-Ferrocenylthienyl)phosphines of type 2-PR2-3-Fc-cC4H2S (R=tBu (2); R=Ph (3); Fc=Fe(η5-C5H4)(η5-C5H5)) were synthesized and the structures of 2 and 3 in the solid state were determined by single X-ray structure analysis. Inter- and intra-molecular T-shaped π⋯π stackings involving cyclopentadienyl and phenyl rings are characteristic for 3. The application of 2 and 3 as ligands in the Pd-catalyzed Suzuki–Miyaura C,C cross-coupling of aryl halides with boronic acids to give the respective biaryls is reported. Electron-rich, electron-poor and sterically hindered substrates could be coupled with high yields at Pd-loadings as low as 0.1mol%.
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