- Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
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As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.
- Li, Zijian,Sun, Wenxuan,Wang, Xianxu,Li, Luyang,Zhang, Yong,Li, Chao
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supporting information
p. 3536 - 3543
(2021/03/08)
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- Disulfide symmetric dimers as stable pre-hapten forms for bioconjugation: A strategy to prepare immunoreagents for the detection of sulfophenyl carboxylate residues in environmental samples
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A convenient, generic synthesis of bioconjugates from haptens with a thiol group has been established. The corresponding haptens are synthesized as stable symmetric dimmers through a disulfide bond that is reduced immediately before conjugation with the a
- Estevez, M.-Carmen,Galve, Roger,Sanchez-Baeza, Francisco,Marco, M.-Pilar
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experimental part
p. 1906 - 1917
(2009/04/08)
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- Stereo- and Regiochemistry in Palladium-Catalyzed Nucleophilic Substitution of Optically Active (E)- and (Z)-Allyl Acetates
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Optically acive (E)- and (Z)-allyl acetates, 3-acetoxy-1-phenyl-1-butene (1) and its regioisomer, 1-acetoxy-1-phenyl-3-butene (2), were allowed to react with sodium dimethyl malonate, sodium acetylacetonate, and sodium methyl acetoacetate in the presence of a palladium catalyst.The reaction of (E)-acetates proceeded with retention of configuration and that of (Z)-acetates proceeded with inversion accompanied by geometrical isomerization from Z to E.The stereochemistry observed in the reaction with phenylzinc bromide was opposite to that with the soft nucleophiles.
- Hayashi, Tamio,Yamamoto, Akihiro,Hagihara, Toshiya
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p. 723 - 727
(2007/10/02)
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