Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201104959 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Dearomative Addition-Hydrogen Autotransfer for Branch-Selective -Heteroaryl C-H Functionalization via Ruthenium-Catalyzed C-C Couplings of Diene Pronucleophiles.
J Am Chem Soc
January 2025
Department of Chemistry, University of Texas at Austin, Austin 78712, Texas, United States.
Article Synopsis
- A new method for C-H functionalization of heteroaryl compounds is introduced, which involves a process called dearomative addition followed by hydrogen autotransfer.
- This process starts with the hydroruthenation of dienes to create allylruthenium nucleophiles, leading to branched C-C coupling products through addition and β-hydride elimination.
- The study also details the formation of enantiomerically enriched heteroarylethyl alcohols and amines through oxidative cleavage and dynamic kinetic asymmetric reduction, supported by density functional theory calculations linking regioselectivities to molecular factors.
Ruthenium-catalyzed three-component tandem remote C-H functionalization of naphthalenes: modular and concise synthesis of multifunctional naphthalenes.
Chem Sci
December 2024
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hubei University Wuhan 430062 P. R. China
The prevalence of naphthalene compounds in biologically active natural products, organic ligands and approved drugs has motivated investigators to develop efficient strategies for their selective synthesis. C-H functionalization of naphthalene has been frequently deployed, but mainly involves two-component reactions, while multiple-component C-H functionalization for the synthesis of naphthalene compounds has thus far proven elusive. Herein, we disclose a versatile three-component protocol for the modular synthesis of multifunctional naphthalenes from readily available simple naphthalenes, olefins and alkyl bromides P(iii)-assisted ruthenium-catalyzed remote C-H functionalization.
View Article and Find Full Text PDFRapid and scalable ruthenium catalyzed meta-C-H alkylation enabled by resonant acoustic mixing.
Commun Chem
December 2024
KAUST Catalysis Center, King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.
Synthetic chemistry approaches for direct C-H bond alkylation offers a promising alternative to traditional functional-group-centered strategies which often involve multi-step procedures and may suffer from a variety of challenges including scalability. Here, we introduce resonant mixing as an efficient method for meta-C-H alkylation of arenes using a Ru-catalyst, avoiding the need for bulk solvents, external temperature, or light. The described methodology is highly rapid, enabling multigram-scale synthesis of meta-alkylation products within a short reaction time and achieving a very high turnover frequency.
View Article and Find Full Text PDFRuthenium-Catalyzed Carbocycle-Selective Hydrogenation of Fused Heteroarenes.
J Am Chem Soc
December 2024
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
The homogeneous catalytic hydrogenation of benzo-fused heteroarenes generally provides partially hydrogenated products wherein the heteroaryl ring is preferentially reduced, such as quinoline hydrogenation, leading to 1,2,3,4-tetrahydroquinoline. Herein, we report a carbocycle-selective hydrogenation of fused -heteroarenes (quinoline, isoquinoline, quinoxaline, etc.) using the Ru complex of a chiral spiroketal-based diphosphine (SKP) as the catalyst, affording the corresponding 5,6,7,8-tetrahydro products in high chemoselectivities.
View Article and Find Full Text PDFRuthenium-Catalyzed α-Regioselective Hydroboration of Allenes.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, 999077, Hong Kong SAR, China.
Hydroboration of allenes is powerful and atom-economic approach to the synthesis of organoboranes, such as the highly versatile allylboranes. However, regarding regiocontrol, existing methods uniformly deliver the boron functionality to the less hindered β- or γ-position, but not the α-position. The latter is particularly challenging for allenes with substantial steric difference between the two terminals and lacking electronic bias (e.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!