C(sp2)-O Bond Formation through a Nickel-Catalyzed Cross-Coupling Reaction in Water Enabled by Micellar Catalysis

A nickel-catalyzed cross-coupling reaction between (functionalized) aryl chlorides and alcohols that results in C(sp(2))-O bond formation is described. This procedure further develops the nickel-catalyzed nucleophilic substitution of aryl chlorides with water. Despite the intolerance of transition-metal catalysis to water, the use of nickel reagents, including their formation and use in an aqueous micellar environment, are discussed herein. The PCy3 ligand, surfactant, and nickel catalyst were all found to be important for C-O bond formation. Various types of aromatic and aliphatic alcohols were tolerated in this reaction, thereby affording a range of ethers in high yields and selectivities.