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Photoinduced Concerted Fragmentation of Alkyl -Phthalimidoyl Oxalates: Mechanisms and Applications.
Org Lett
December 2024
School of Pharmaceutical and Chemical Engineering and Institute for Advanced Studies, Taizhou University, Taizhou 318000, China.
In this work, we used experiments and density functional theory calculations to investigate the mechanism and driving forces of the reductive fragmentation of NHPI esters. Mechanistic studies suggest that the fragmentation behavior of the NHPI ester is influenced not only by the electronic nature of the substituent group but also by the stability of the radical intermediate. To further investigate this transformation, we next examined the aminoalkoxycarbonylation of alkenes using alkyl -phthalimidoyl oxalates.
View Article and Find Full Text PDFExpanding the reaction toolbox for nanoscale direct-to-biology PROTAC synthesis and biological evaluation.
RSC Med Chem
December 2024
Modality Platform Technologies, GSK Stevenage SG1 2NY UK
High-throughput chemistry (HTC) and direct-to-biology (D2B) platforms allow for plate-based compound synthesis and biological evaluation of crude mixtures in cellular assays. The rise of these workflows has rapidly accelerated drug-discovery programs in the field of targeted protein degradation (TPD) in recent years by removing a key bottleneck of compound purification. However, the number of chemical transformations amenable to this methodology remain minimal, leading to limitations in the exploration of chemical space using existing library-based approaches.
View Article and Find Full Text PDFA Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides.
J Org Chem
December 2024
Department of Chemistry, Oklahoma State University, 107 Physical Sciences, Stillwater, Oklahoma 74078, United States.
While charge-transfer complexes involving halogen-bonding interactions have emerged as an alternative strategy for the photogeneration of carbon radicals, examples using (fluoro)alkyl bromides are limited. This report describes a dual catalytic approach for radical generation from α-bromodifluoroesters and amides under visible-light irradiation. Mechanistic studies suggest that the reaction proceeds through bromide displacement using a catalytic iodide salt, generating a C-I bond that can be engaged by our halogen-bonding photocatalysis platform.
View Article and Find Full Text PDFHydroalkylation of Vinylarenes by Transition-Metal-Free In Situ Generation of Benzylic Nucleophiles Using Tetramethyldisiloxane and Potassium tert-Butoxide.
Angew Chem Int Ed Engl
December 2024
University of Ottawa, Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, k1n6n5, Ottawa, CANADA.
Hydrosilanes and Lewis bases are known to promote various reductive defunctionalizations, rearrangements, and silylation reactions, facilitated by enigmatic silicon/Lewis base-derived reactive intermediates. Despite the wide variety of transformations enabled by this reagent combination, no examples of intermolecular C(sp3)-C(sp3) forming reactions have been reported. In this work, we've identified 1,1,3,3-tetramethyldisiloxane (TMDSO) and KOtBu as a unique reagent combination capable of generating benzylic nucleophiles in-situ from styrene derivatives, which can subsequently react with alkyl halides to give a new C(sp3)-C(sp3) linkage via formal hydroalkylation.
View Article and Find Full Text PDFInsight into the Thermal Washing Mechanism of Sodium Lignosulfonate Alkyl/Sodium Persulfate Compound on Oily Sludge.
Int J Mol Sci
November 2024
Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, School of Light Industrial and Food Engineering, Guangxi University, Nanning 530004, China.
Article Synopsis
- The study investigates the effectiveness of using sodium persulfate (SD) and sodium lignosulfonate surfactant in thermally washing oily sludge to improve remediation methods.
- It evaluates the impact of various reaction conditions on the breakdown of different hydrocarbon types (saturated, aromatic, resins, and asphaltenes) in oily sludge.
- Results showed that while SD effectively degrades these hydrocarbons, sodium hydroxide acts as a catalyst, and lignosulfonate aids in the removal process by lowering the solution's surface tension.
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