A process for conducting
coupling reactions of
aryl halides with unsaturated
silanes is described. The processes use N-heterocyclic carbenes as ancillary ligands in these
coupling reactions. A
coupling of an
aryl halide with an unsaturated
silane can be carried out by mixing, in a
liquid medium, at least one strong base; at least one
aryl halide or aryl pseudohalide in which all substituents are other than silyl groups, wherein the
aryl halide has, directly bonded to the aromatic ring(s), at least one
chlorine atom,
bromine atom, or
iodine atom; at least one
silane wherein the
silicon atom is
quaternary, wherein one group bound to the
silicon atom is unsaturated at the alpha or beta position, and wherein each of the remaining groups bound to the
silicon atom is a saturated hydrocarbyl or a saturated hydrocarbyloxy group; at least one
nickel,
palladium, or
platinum compound, wherein the formal
oxidation state of the
metal is zero or two; and at least one N-heterocyclic
carbene. One preferred type of N-heterocyclic
carbene is an imidazoline-2-ylidene of the formulawherein R1 and R2 are each, independently,
alkyl or aryl groups having at least 3 carbon atoms, R3 and R4 are each, independently, a
hydrogen atom, a
halogen atom, or a hydrocarbyl group.