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Creators/Authors contains: "Zavalij, Peter"

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  1. We report an investigation of the complexation between a water soluble pillararene host (WP6) and a panel of hydrophobic cationic guests (G1–G20) by a combination of 1 H NMR spectroscopy and isothermal titration calorimetry in phosphate buffered saline. We find that WP6 forms 1 : 1 complexes with K a values in the 10 4 –10 9 M −1 range driven by favorable enthalpic contributions. This thermodynamic dataset serves as blinded data for the SAMPL9 challenge.
    Free, publicly-accessible full text available January 17, 2023
  2. Free, publicly-accessible full text available October 4, 2022
  3. A highly chemoselective iron-catalyzed three-component dicarbofunctionalization of unactivated olefins with alkyl halides (iodides and bromides) and sp 2 -hybridized Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp 2 -hybridized nucleophiles (electron-rich and electron-deficient (hetero)aryl and alkenyl Grignard reagents), alkyl halides (tertiary alkyl iodides/bromides and perfluorinated bromides), and unactivated olefins bearing diverse functional groups including tethered alkenes, ethers, protected alcohols, aldehydes, and amines to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C–C bonds.
  4. A disulfide made by oxidation of 8-thioguanosine is a supergelator. The hydrogels are redox-responsive, as they disassemble upon either reduction or oxidation of the S–S bond. We also identified this disulfide, and 2 other compounds, as intermediates in oxidative desulfurization of 8-thioG to guanosine.