Synthesis of aryl coupled bis phenoxides and their use in olefin polymerization catalyst systems with activator-supports

A method of making a transition metal bis(phenolate) compound having the formula:

• the method comprising:
• (i) contacting a phenol compound having the formula:
• with
• (a) zinc metal;
• (b) a zinc-containing transfer agent;
• or
• (c) a halogen transfer agent and a zinc transfer compound;
• in the presence of a reaction solvent to form a first mixture;
• (ii) contacting the first mixture with a palladium cross-coupling catalyst system and a substituted or unsubstituted, saturated or unsaturated, C4 to C8 heterocyclic compound having the formula:
• to form a ligand reaction mixture comprising a bis(phenol) ligand compound having formula (II):
• and
• (iii) contacting the ligand compound having formula (II) with M(X)(X)(X)(X), optionally in the presence of a second solvent, to form a transition metal compound reaction mixture comprising the transition metal bis(phenol) compound having formula (I);
• wherein:
• R2, R3, R4, and R5 independently are H or a C1 to C18 hydrocarbyl or halogenated hydrocarbyl group;
• is a substituted or unsubstituted, saturated or unsaturated, C4 to C8 heterocyclic group, wherein each RA independently is a C1 to C18 hydrocarbyl or halogenated hydrocarbyl group, and m is 0, 1, 2, or 3;
• each XA independently is Cl, Br, or I;
• M is Ti, Zr, or Hf;
• each X independently is a monoanionic ligand;
• and
• each L independently is a neutral ligand, wherein n is 0, 1 or 2.