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The reaction of 2,2′-diiodo-1,1′-biphenyl ( 1a ) with ethynyl ferrocene ( 2 ) gave trace amounts of the expected 2,2′-bis(ferrocenylethynyl)-1,1′-biphenyl ( 3 ) together with 9-(ferrocenyl(ferrocenylethynyl)methylene)-9 H -fluorene ( 4 ), formed via a cyclization process during the Sonogashira cross-coupling reaction, as the major product. In contrast, a similar reaction of the 2,2′-diiodo-1,1′-diphenyl ether analogue with  2  gave the anticipated 2,2′-bis(ferrocenylethynyl) substituted product ( 11 ). Reaction of  11  with tetracyanoethylene gave its bis-[2 + 2] cycloaddition product in high yield ( 12 ), while the alkynyl motif in fluorenylidene  4  proved to be inert towards such reactions. Studies of the mechanism leading to formation of  4  using a Pd/dppf (dppf = 1,1′-bis(diphenylphosphino)ferrocene) catalyst combination allowed for isolation of a {C = C(Fc)–PdI(dppf)} intermediate ( 13 ), which was structurally characterized by single crystal X-ray diffraction. Electrochemical investigations of  4 ,  11 ,  12  and  13  revealed a series of essentially ferrocene-based oxidation processes, which in the case of  4  and  11  could be better resolved using a non-coordinating anion based electrolyte. Electronic structure studies at the DFT level (B3LYP/def2-TZVP/CPCM(CH 2 Cl 2 ) suggest that the first oxidation event in  4  can be assigned to the vinyl-bonded ferrocenyl moiety.

journal of coordination chemistry

Structural characterization of ((9-fluorenylidene) (ferrocenyl)methyl)palladium iodide as the catalytic intermediate in the synthesis of 9-(ferrocenyl (ferrocenylethynyl)methylene)-9 H -fluorene