- Photoredox/Nickel-Catalyzed Single-Electron Tsuji–Trost Reaction: Development and Mechanistic Insights
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A regioselective, nickel-catalyzed photoredox allylation of secondary, benzyl, and α-alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DFT and DLPNO-CCSD(T)] support the mechanistic hypothesis of a Ni0 to NiII oxidative addition pathway followed by radical addition and inner-sphere allylation.
- Matsui, Jennifer K.,Gutiérrez-Bonet, álvaro,Rotella, Madeline,Alam, Rauful,Gutierrez, Osvaldo,Molander, Gary A.
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supporting information
p. 15847 - 15851
(2018/11/23)
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- Perfume base composition
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The present invention relates to a perfume base composition comprising a carrier and a benzyl-substituted cyclohexanol having formula (1), wherein the dashed line denotes an optional double bond and the benzyl group is in the 2-, 3- or 4-position of the c
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- Rearrangement of allylic and propargylic alcohols catalyzed by the combined use of tetrabutylammonium perrhenate(VII) and p-toluenesulfonic acid
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Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, α,β-unsaturated carbonyl compounds, while β,γ-unsaturated ketones are obtained as main products by the reaction in refluxing 1,2-dichloroethane. The application of this catalytic system is also described for the preparation of some synthetic intermediates.
- Narasaka,Kusama,Hayashi
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p. 2059 - 2068
(2007/10/02)
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- Rearrangement of Allylic and Propargylic Alcohols Catalyzed by the Combined Use of Tetrabutylammonium Perrhenate(VII) and p-Toluenesulfonic Acid
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Allylic rearrangement and/or dehydration of allylic alcohols proceed by the use of a catalytic amount of tetrabutylammonium perrhenate and p-toluenesulfonic acid.Treatment of propargylic alcohols with the above reagents affords the rearranged products, α,β-unsaturated carbonyl compounds.
- Narasaka, Koichi,Kusama, Hiroyuki,Hayashi, Yujiro
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p. 1413 - 1416
(2007/10/02)
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