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Base-Free Borylation of Aryl Halides Enabled by Zn-Promoted Halide Abstraction.
Org Lett
December 2024
Department of Chemistry, The University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States.
Herein, we report the palladium-catalyzed borylation of aryl halides (iodides or bromides) under base-free conditions utilizing a commercially available Lewis acidic mediator, Zn(OTf). Under these conditions, an array of electronically and functional-group-diverse aryl iodides and bromides undergo borylation to afford the corresponding aryl boronic esters in ≤82% isolated yields. Mechanistic investigations are consistent with Zn(OTf) enabling transmetalation between a cationic Pd(II)-Ar intermediate and Bpin via halide abstraction.
View Article and Find Full Text PDFConcise Asymmetric Total Syntheses of (+)-Dihydropleurotinic Acid and (-)-Pleurotin, Enabling Rapid Late-Stage Diversification.
JACS Au
November 2024
Laboratory of Medicinal Chemical Biology, Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren'ai Road, Suzhou 215123, China.
(-)-Pleurotin () and (+)-dihydropleurotinic acid () are benzoquinone meroterpenoids isolated from fungal sources with powerful antitumor and antibiotic activities. Concise asymmetric total syntheses of the stereochemically pure (+)-dihydropleurotinic acid () and (-)-pleurotin () from the chiral pool ()-Roche ester-derived vinyl bromide have been achieved in 12 and 13 longest linear steps, respectively. The key transformations feature a Michael addition/alkylation cascade reaction to forge three contiguous stereocenters matched with the natural products, a PtO-catalyzed stereoselective reduction of olefin to generate the correct stereocenter at C3, a palladium-catalyzed Negishi cross-coupling between triflate and zinc reagent to introduce the redox-sensitive para-quinone moiety, and a hydroboration/copper-catalyzed carboxylation sequence to incorporate the vital carboxyl group.
View Article and Find Full Text PDFExploring C2 and N Substituent Effects on Truncated 4'-Thioadenosine Derivatives as Dual A and A Adenosine Receptor Ligands.
ChemMedChem
October 2024
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 08826, Republic of Korea.
Based on high binding affinity of truncated 2-hexynyl-4'-thioadenosine (3 a) at both A adenosine receptor (AR) and A AR, we explored structure-activity relationship (SAR) of the C2-substitution by altering chain length of the 2-hexynyl moiety, thereby evaluating the hydrophobic pocket size. A series of truncated N-substituted 4'-thioadenosine derivatives with C2-alkynyl substitution were successfully synthesized from D-mannose, using a palladium-catalyzed Sonogashira coupling reaction as the key step, whose structures were confirmed by the X-ray crystal structure of 4 h. As the size of the alkynyl group at the C2-position increased, the binding affinity improved; however, when the substituted group was larger than hexynyl, the binding affinity decreased.
View Article and Find Full Text PDFNitrogen-Bridged Fused-Ring Nonacyclic and Heptacyclic A-D-A Acceptors for Organic Photovoltaics.
ACS Appl Mater Interfaces
October 2024
Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 University Road, Hsinchu, Taiwan 30010.
In this work, we designed two nitrogen-bridged fluorene-based heptacyclic FNT and nonacyclic FNTT ladder-type structures, which were constructed by one-pot palladium-catalyzed Buchwald-Hartwig amination. FNT and FNTT were further end-capped by FIC acceptors to form two FNT-FIC and FNTT-FIC non-fullerene acceptors (NFAs), respectively. The two NFAs exhibit more red-shifted absorption and higher crystallinity compared to those of the corresponding carbon-bridged FCT-FIC and FCTT-FIC counterparts.
View Article and Find Full Text PDFDFT Investigation on Palladium-Catalyzed [2 + 2 + 1] Spiroannulation between Aryl Halides and Alkynes: Mechanism, Base Additive Role, and Solvent and Ligand Effects.
J Phys Chem A
October 2024
Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, China.
Article Synopsis
- Transition metal-catalyzed spiroannulations are effective for building important spirocyclic structures, though their microscopic mechanisms aren't fully understood.
- A study using density functional theory (DFT) examined a palladium-catalyzed spiroannulation, identifying a sequence of steps that lead to the formation of the spiro[4,5]decane product, with the C-Br oxidative addition as the rate-determining step.
- The computational predictions regarding the reaction kinetics, solvent effects, and base contributions align well with experimental outcomes, indicating potential for improved catalytic processes and new designs in these types of reactions.
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