Precatalyst scaffolds for cross-coupling reactions, and methods of making and using same

A method of promoting a reaction between a first reagent and a second reagent, wherein the first reagent is an aromatic or heteroaromatic amine and the second reagent is an aromatic or heteroaromatic halide, tosylate, triflate, mesylate, sulfamate or carbamate, the method comprising contacting the first reagent and the second reagent in the presence of at least one of (i) and (ii):

• (i) a ligand (L) and a precatalyst of formula (I), or a salt or solvate thereof:
• and
• (ii) a precatalyst of formula (II), or a salt or solvate thereof:
• wherein:
• each occurrence of M is independently selected from the group consisting of Pd, Pt, and Ni;
• each occurrence of X is independently a ligand selected from the group consisting of halide, trifluoromethanesulfonate (triflate), tosylate, mesylate, tetrafluoroborate, tetraphenylborate, hexafluorophosphine, acetate, trifluoroacetate, acetonitrile, tetrahydrofuran, and dichloromethane;
• each occurrence of R is independently selected from the group consisting of alkyl and substituted alkyl;
• with the proviso that each of the 5-membered rings is substituted with at least one independently selected R;
• and
• Z is CH or CR;
• L is selected from the group consisting of a monodentate phosphine ligand, a bidentate phosphine ligand, and an N-heterocyclic carbene ligand;
• and
• n is 1, 2, or 3.