Catalyzed coupling reactions of aryl halides with silanes

A process for conducting a reaction in which a heterocoupled product is formed, which process comprises mixing, in a liquid medium,

• i) at least one strong base;
• ii) 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 halogen atom selected from the group consisting of a chlorine atom, a bromine atom, and an iodine atom;
• iii) 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;
• iv) at least one metal compound comprising at least one metal atom selected from nickel, palladium, and platinum, wherein the formal oxidation state of the metal is zero or two;
• and
• v) at least one N-heterocyclic carbene selected from the group consisting of an imidazoline-2-ylidene wherein at least the 1 or the 3 position is substituted by a secondary or tertiary group which has at least three atoms, or a protonated salt thereof;
• an imidazolidine-2-ylidene wherein at least the 1 or the 3 position is substituted by a secondary or tertiary group which has at least three atoms, or a protonated salt thereof;
• a bis(imidazoline-2-ylidene) wherein a bridging moiety is bound to one nitrogen atom of each ring, and wherein the remaining two nitrogen atoms are each, independently, substituted by a secondary or tertiary group which has at least free atoms, or a protonated salt thereof;
• and a bis(imidazolidine-2-ylidene) wherein a bridging moiety is bound to one nitrogen atom of each ring, and wherein the remaining two nitrogen atoms are each, independently, substituted by a secondary or tertiary group which has at least three atoms, or a protonated salt thereof;
• and mixtures of two or more of the foregoing.