Aryl halide cross-coupling method and product made therefrom

14:

• An aryl halide cross-coupling method, comprising:
• reacting the aryl halide with a compound comprising at least one of a boronic acid, a terminal alkyne, and an alkene in the presence of a solvent, a base, and a solid-supported catalyst to form a palladium cross-coupling product,
• wherein the solid-supported catalyst, comprises:
• a catalytic metal in the form of a Pd+2 species having the formula PdZ2, wherein Z is selected from the group consisting of —Cl, —I, —Br, —OAc and —OTf, and
• a solid-supported ligand of formula (I)
• wherein the nitrogen atoms of the two oxazoline heterocycles of the solid-supported ligand chelate the catalytic metal;
• and
• wherein R1, R2, R3 and R4 are independently —H, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;
• each R5 and R6 is independently —H, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;
• X is O, NH, or S;
• and
• wherein SS is a solid resin bead with the proviso that the solid resin bead is not silica.

15:

• The method of claim 14, wherein
• each R1 and R2 is —CH3;
• each R3, R4, R3, and R6 is —H;
• X is O;
• and
• the Pd+2 species having the formula PdZ2 is PdCl2.

16:

• The method of claim 14, further comprising:
• separating the solid-supported catalyst from the palladium cross-coupling product to recover the solid-supported catalyst;
• and
• reusing the solid-supported catalyst in at least 2 reaction cycles with a less than 10% decrease in at least one selected from the group consisting of a turnover number and a turnover frequency.