37471-41-3Relevant articles and documents
The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols
He, Zhen,Pulis, Alexander P.,Procter, David J.
supporting information, p. 7813 - 7817 (2019/05/15)
A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.
Gold-catalyzed carbene transfer to alkynes: Access to 2,4-disubstituted furans
Kramer, Soren,Skrydstrup, Troels
supporting information; experimental part, p. 4681 - 4684 (2012/06/30)
Furans of gold: The first example of a gold-catalyzed intermolecular addition of carbon ylides to terminal alkynes is reported (see scheme; DCE=dichloroethane, Tf=trifluoromethanesulfonyl). Subsequent intramolecular trapping of the generated gold carbene completes a formal [3+2] cycloaddition, which represents a novel synthesis of 2,4-disubstituted furans. Copyright
A new route for generation of α-λ3-iodanyl ketones via ester exchange of (Z)-(β-acetoxyvinyl)-λ3-iodanes: Their nucleophilic substitutions with halides and sulfur and phosphorus nucleophiles
Ochiai, Masahito,Nishitani, Junichi,Nishi, Yoshio
, p. 4407 - 4413 (2007/10/03)
An efficient method for generation of α-λ3-iodanyl ketones from (Z)-(2-acetoxyvinyl)(phenyl)-λ3-iodanes was developed. The method involves ester exchange of (Z)-2-acetoxyvinyl-λ3-iodanes with methanol in the presence of triethylamine. α-λ3Iodanyl ketones react with a variety of nucleophiles such as halides, thiols, phosphines, phosphinic acids, and phosphates, under the conditions which produce α-functionalized carbonyl compounds probably via an SN2 pathway.