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Electrochemical Dicarboxylation of Vinyl Epoxide with CO2 for the Facile and Selective Synthesis of Diacids.
Angew Chem Int Ed Engl
December 2024
East China Normal University, School of Chemistry and Molecular Engineering, 3663 N. Zhongshan Rd., 200062, Shanghai, CHINA.
We present a novel electrochemical dicarboxylation of epoxides with CO2, characterized by the cleavage of two C-O single bonds. Not only are vinyl epoxides viable, but cyclic carbonates also serve as effective substrates, facilitating the synthesis of E-configured adipic and octanedioic acids with high chemo-, regio-, and stereoselectivity. The synthetic practicality is further highlighted by the diverse functionalizations of the resulting multifunctional diacids.
View Article and Find Full Text PDFPhotoredox/Cobalt-Catalyzed Chemo-, Regio-, Diastereo- and Enantioselective Reductive Coupling of 1,1-Disubstituted Allenes and Cyclobutenes.
Angew Chem Int Ed Engl
December 2024
Shanghai Institute of Organic Chemistry, State Key Lab of Organometallic Chemistry, 345 Lingling Road, 200032, Shanghai, CHINA.
A dual photoredox/cobalt-catalyzed protocol for chemo-, regio-, diastereo- and enantioselective reductive coupling of 1,1-disubstituted allenes and cyclobutenes through chemo-, regio-, diastereo- and enantioselective oxidative cyclization followed by stereoselective protonation promoted by a chiral phosphine-cobalt complex is presented. Such process represents an unprecedented reaction pathway for cobalt catalysis that enables selective transformation of the less sterically congested alkenes of 1,1-disubstituted allenes with cyclobutenes, incorporating a broad scope of tetrasubstituted alkenes into the cyclobutane scaffolds in up to 86% yield, >98:2 chemo- and regioselectivity, >98:2 dr and >99.5:0.
View Article and Find Full Text PDFInvestigations on the Synthesis of Chiral Ionic-Liquid-Supported Ligands and Corresponding Transition-Metal Catalysts: Strategy and Experimental Schemes.
Molecules
November 2024
Collaborative Innovation Center for Efficient Utilization of Water Resources, North China University of Water Resources and Electric Power, Zhengzhou 450046, China.
Ionic liquids have been utilized in numerous significant applications within the field of chemistry, particularly in organic chemistry, due to their unique physical and chemical properties. In the realm of asymmetric transition-metal-catalyzed transformations, chiral ionic-liquid-supported ligands and their corresponding transition-metal complexes have facilitated these processes in unconventional solvents, especially ionic liquids and water. These innovative reaction systems enable the recycling of transition-metal catalysts while producing optically active organic molecules with comparable or even higher levels of chemo-, regio-, and stereoselectivity compared to their parent catalysts.
View Article and Find Full Text PDFSelective [3 + 2] C-H/C-H Alkyne Annulation via Dual (Distal) C-H Bond Activation Relay: A Novel Therapeutic Quinazolone-Tethered Benzofulvenes for Oral Cancer.
JACS Au
November 2024
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER) - Ahmedabad, Palaj, Gandhinagar 382355, Gujarat, India.
Article Synopsis
- The text discusses a new method for activating distal C-H bonds to create benzofulvenes, which are compounds formed through a [3 + 2] reaction involving palladium catalysis, overcoming traditional bond activation challenges.
- This innovative approach involves concurrent activation of both β-C(benzylic)-H and δ-C(aryl)-H bonds and leads to the formation of novel chemical entities with promising anticancer properties.
- In studies, these new compounds were found to effectively target oral squamous cell carcinoma (OSCC) by arresting the cell cycle at the S-phase and activating various apoptosis pathways, indicating their potential as effective chemotherapy options.
Intramolecularly remote functional group migration reactions involving free radicals.
Chem Commun (Camb)
December 2024
Frontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
The application of rearrangement reactions offers opportunities for the efficient construction of complex molecules that are challenging to obtain through conventional synthetic methods. However, the development of radical-mediated rearrangements has lagged far behind that of ionic-type rearrangements, due to the uncontrollability of radical species. Along with the recent renaissance in radical chemistry, radical-mediated functional group migration (FGM) reactions provide a versatile platform for the selective incorporation of functional groups across different molecular distances, enabling the construction of intricate molecular architectures.
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