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Standardized Approach for Diversification of Complex Small Molecules via Aryl Thianthrenium Salts.
J Am Chem Soc
January 2025
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, Mülheim an der Ruhr 45470, Germany.
Thianthrenation is a useful strategy for the late-stage diversification of complex small molecules owing to the positional selectivity and the synthetic versatility of thianthrenium salts as electrophilic linchpins. However, substrate-dependent identification of suitable reaction conditions for thianthrenation can be difficult. Reported reaction conditions for the functionalization of thianthrenium salts vary significantly and, in some instances, lack robustness and practicality.
View Article and Find Full Text PDFCascade Aza-Prins/Friedel-Crafts Reaction of Homocinnamyloxycarbamate and Aromatic Aldehydes Yielding Aromatic Ring-Annulated Hydrocyclopenta-1,2-oxazinane.
J Org Chem
January 2025
Applied Chemistry and Chemical Engineering, Graduate School of Engineering, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
The cascade aza-Prins/Friedel-Crafts reaction of homocinnamyloxycarbamate with electron-rich aromatic aldehydes has been successfully established. Most of the aromatic aldehydes react with the carbamate stereoselectively to generate -hydroindeno-1,2-oxazinanes. However, the cascade reactions of benzaldehydes bearing two methoxy groups at the -positions exhibit a unique stereochemical profile.
View Article and Find Full Text PDFContinuous-Flow Ritter Reaction for Sustainable Amide Synthesis Using a Recyclable -Phenolsulfonic Acid-Formaldehyde Resin Catalyst.
J Org Chem
January 2025
RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan.
Herein, a rapid and efficient continuous-flow synthesis of amides is described. The Ritter reaction, catalyzed by a reusable solid acid catalyst composed of -phenolsulfonic acid-formaldehyde resin (PAFR II), was used to convert nitriles and alcohols to amides in up to 90% yield. The continuous-flow system facilitates short reaction times and maintains activity for several weeks.
View Article and Find Full Text PDFCarbon-Bromide Bond Activation by Bidentate Halogen, Chalcogen, Pnicogen, and Tetrel Bonds.
J Phys Chem A
December 2024
College of Chemistry and Materials Science, Hebei Key Laboratory of Inorganic Nano-Materials, Hebei Normal University, Shijiazhuang 050024, China.
Halogen, chalcogen, pnictogen, and tetrel bonds in organocatalysis have gained noticeable attention. In this work, carbon-bromide bond activation in the Ritter reaction by bidentate imidazole-type halogen, chalcogen, pnicogen, and tetrel bond donors was studied by density functional theory. All of the above four kinds of catalysts exhibited excellent catalytic performance.
View Article and Find Full Text PDFMeta-Dimethylation of Arenes via Catellani Reaction from Aryl Thianthrenium Salts.
Angew Chem Int Ed Engl
November 2024
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470, Mülheim an der Ruhr, Germany.
Here we report the reaction of aryl thianthrenium salts that allows selective functionalization of the meta position of arenes. The combination of a site-selective thianthrenation with a Catellani reaction provides access to 3,5-dimethylated arenes. The developed reaction is complementary to the previously discovered reductive ipso-alkylation of aryl thianthrenium salts and extends the possibilities for late-stage methylation of arenes with a single aryl thianthrenium salt.
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