Weix, D., and R. Shrestha. Reductive Conjugate Addition of Haloalkanes to Enones To Form Silyl Enol Ethers. Org. Lett., 2769.
| Abstract | A new method is presented for tandem reductive conjugate addition and silyl enol ether formation from cyclic and acyclic enones and enals in the presence of a Mn reductant, a Ni(terpyridine) catalyst, and a trialkylchlorosilane. The addition of secondary, tertiary, and hindered primary haloalkanes Is demonstrated. Preliminary studies on the mechanism show that the intermediacy of L1(Ni)(eta(3)-1-triethylsilyloxyalkenyl)X or in-situ-formed RMnX is unlikely. |
| Keywords | activated olefins, alkyl-halides, allylic grignard-reagents, aryl halides, bicyclic ketones, carbonyl-compounds, cobalt, cross-coupling reactions, nickel-complexes, organic halides |
| DOI | 10.1021/ol200881v |