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Reductive Conjugate Addition of Haloalkanes to Enones To Form Silyl Enol Ethers

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https://figshare.com/articles/dataset/Reductive_Conjugate_Addition_of_Haloalkanes_to_Enones_To_Form_Silyl_Enol_Ethers/2650915
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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)(η3-1-triethylsilyloxyalkenyl)X or in-situ-formed RMnX is unlikely.
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2011-05-20
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