Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Despite a few successful examples, controlling the enantioselectivity in the asymmetric synthesis of non--symmetric biaryldiols has long been challenging. To address the issues of enantioselectivity and regioselectivity, we introduced a novel organoelectrocatalytic strategy enabling asymmetric aryl-aryl dehydrogenative cross-coupling reactions. Using this approach, valuable non--symmetric biaryldiols were obtained in up to 95% yields and 97% enantiomeric excesses (s), and these compounds could be further applied as versatile ligands in asymmetric reactions. Detailed mechanistic studies supported a sequential diradical cross-coupling followed by a central-to-axial chirality conversion pathway.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jacs.4c16426 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electrochemical dehydrogenative intramolecular C-C coupling for expedient carbazole synthesis.
Chem Commun (Camb)
September 2025
Institute of Sustainability for Chemicals, Energy and Environment (ISCE2), Agency for Science, Technology and Research (A*STAR), 1 Pesek Road, Singapore 627833, Republic of Singapore.
An electrochemical method for carbazole synthesis dehydrogenative aryl-aryl coupling of arylamines under metal-free conditions at ambient temperature is presented. The reactivity of arylamines is rationalised by cyclic voltammetry and density functional theory (DFT) studies to provide a preliminary understanding of the observed regioselectivity.
View Article and Find Full Text PDFRapid access to fluorene-9-carboxamides through palladium-catalysed cross-dehydrogenative coupling.
Org Biomol Chem
August 2025
Catalytic Hydrogenation Research Center, State Key Laboratory of Green Chemical Synthesis and Conversion, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Herein, we describe a facile synthesis of fluorene-9-carboxamides through a palladium-catalysed intramolecular cross-dehydrogenative aryl-aryl coupling reaction. The reaction features mild reaction conditions, a broad substrate scope, and simplicity of operation, constituting an interesting shortcut to access fluorene compounds.
View Article and Find Full Text PDFSynthesis of Non-Symmetric Biaryldiols via Organo-Electro Catalyzed Aryl-Aryl Dehydrogenative Cross-Coupling.
J Am Chem Soc
March 2025
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China.
Despite a few successful examples, controlling the enantioselectivity in the asymmetric synthesis of non--symmetric biaryldiols has long been challenging. To address the issues of enantioselectivity and regioselectivity, we introduced a novel organoelectrocatalytic strategy enabling asymmetric aryl-aryl dehydrogenative cross-coupling reactions. Using this approach, valuable non--symmetric biaryldiols were obtained in up to 95% yields and 97% enantiomeric excesses (s), and these compounds could be further applied as versatile ligands in asymmetric reactions.
View Article and Find Full Text PDFStepwise on-surface synthesis of nitrogen-doped porous carbon nanoribbons.
Commun Chem
February 2024
Center for Soft Condensed Matter Physics & Interdisciplinary Research, School of Physical Science and Technology, Soochow University, Suzhou, 215006, China.
Precise synthesis of carbon-based nanostructures with well-defined structural and chemical properties is of significance towards organic nanomaterials, but remains challenging. Herein, we report on a synthesis of nitrogen-doped porous carbon nanoribbons through a stepwise on-surface polymerization. Scanning tunneling microscopy revealed that the selectivity in molecular conformation, intermolecular debrominative aryl-aryl coupling and inter-chain dehydrogenative cross-coupling determined the well-defined topology and chemistry of the final products.
View Article and Find Full Text PDFSynthesis of Aporphine Analogues via Palladium-Catalyzed Intramolecular Aryl-Aryl Dehydrogenative Coupling.
J Org Chem
October 2021
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, People's Republic of China.
Article Synopsis
- This study discusses a new method for connecting two inactive aryl C-H bonds to create aporphine analogues using an intramolecular dehydrogenative coupling reaction.
- The reaction utilizes palladium as a catalyst and allows for the activation of C-H bonds, making it a unique approach in synthetic chemistry.
- Additionally, the resulting products from this coupling can be further utilized to synthesize natural compounds such as aporphine and zenkerine.