Synthesis, Structure, and Reactivity of a Gold Carbenoid Complex That Lacks Heteroatom Stabilization.

Angewandte Chemie (International ed. in English)

PubMedID: 24990811

Harris RJ, Widenhoefer RA. Synthesis, Structure, and Reactivity of a Gold Carbenoid Complex That Lacks Heteroatom Stabilization. Angew Chem Int Ed Engl. 2014;.
Hydride abstraction from the neutral gold cycloheptatrienyl complex [(P)Au(?(1) -C7 H7 )] (P=P(tBu)2 (o-biphenyl)) with triphenylcarbenium tetrafluoroborate at -80?°C led to the isolation of the cationic gold cycloheptatrienylidene complex [(P)Au(?(1) -C7 H6 )](+) BF4 (-) in 52?% yield, which was characterized in solution and by single-crystal X-ray diffraction. This cycloheptatrienylidene complex represents the first example of a gold carbenoid complex that lacks conjugated heteroatom stabilization of the electron-deficient C1 carbon atom. The cycloheptatrienylidene ligand of this complex is reactive; it can be reduced by mild hydride donors, and converted to tropone in the presence of pyridine N-oxide.