Copper-catalyzed conjugate addition to enones forms valuable silyl enol ether products, but has limited functional group tolerance due to the reactive organocuprate. An alternative approach utilizing cross-electrophile coupling will be presented, in which a nickel and bipyridine catalyst react with the a,�-unsubstituted carbonyl and trialkylchlorosilane to form a nickel(siloxyallyl)complex which subsequently reacts with an aryl halide. The mild conditions allow for wide substrate scope including acidic protons (-NHCOCF3) and electrophilic carbons (aldehydes and ketones). Recent advancements will be discussed.  

Nickel-catalyzed cross-electrophile coupling to afford conjugate addition type products

248th National Meeting (2014)

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