Transition metal catalyzed Kumada, Suzuki, and Negishi cross-coupling reactions have become a staple of organic synthesis and are frequently the most practical strategy for synthesis of medicinal agents and fine chemicals. Catalysts based on the precious metal palladium are commonly used in cross-coupling reactions. Replacing palladium catalysts with nickel catalysts is an active area of research, as such advances present significant benefits including decreasing the environmental impact of the transformation and new mechanisms for control of stereochemistry in construction of Csp3–Csp3 bonds. Nickel-catalyzed stereocontrolled cross-coupling reactions of secondary benzylic ethers with a variety of aliphatic and aryl Grignard reagents as well as mechanistic insights of the reaction and major side pathways will be presented. The method is highly stereospecific and proceeds with inversion at the benzylic carbon. Several compounds synthesized by this method exhibit selective inhibition of MCF-7 breast cancer cells.

Stereospecific nickel-catalyzed cross-coupling of benzylic ethers with Grignard reagents

249th National Meeting (2015)

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