Hiyama Reactions of Activated and Unactivated Secondary Alkyl Halides Catalyzed by a Nickel/Norephedrine Complex

An active partner: Nickel in combination with an amino alcohol ligand (norephedrine) was found to provide the most versatile and efficient catalyst for Hiyama cross-coupling reactions of alkyl electrophiles that has been described to date. Unprecedented Hiyama reactions of activated secondary alkyl bromides were achieved, as were the first Hiyama couplings of (activated) alkyl chlorides (see scheme, X=Br, Cl; HMDS=1,1,1,3,3,3-hexamethyldisilazane, DMA=N,N-dimethylacetamide).