Conversion of methane to ethylene using an Ir complex and phosphorus ylide as a methylene transfer reagent.

Cp*(Me3P)Ir(CH3)(OTf), a complex known to reversibly activate CH4 and other hydrocarbons under mild conditions, reacts with the phosphorus ylide H2CPPh3 in THF to afford two major species [Cp*(Me3P)(Ph3P)Ir(CH2CH3)][OTf] and [Cp*(Me3P)Ir(H)(eta(2)-CH2CH2)][OTf]. Insertion of the ylide methylene group can also occur with Cp*(Me3P)Ir(Ph)(OTf) to afford the benzyl [Cp*(Me3P)(Ph3P)Ir(CH2-Ph)][OTf]. Theoretical studies suggest the intermediacy of an Ir(III)= CH2 species.