The catalytic acceptorless dehydrogenation (CAD) is an attractive synthetic route to unsaturated compounds because of its high atomic efficiency. Here we report electrochemical acceptorless dehydrogenation of N-heterocycles to obtain quinoline or indole derivatives using metal-organic layer (MOL) catalyst. MOL is the two-dimensional version of metal-organic frameworks (MOF), and it can be constructed on conductive multi-walled carbon nanotubes via facile solvothermal synthesis to overcome the conductivity constraint for MOFs in electrocatalysis. TEMPO-OPO was incorporated into the system through a ligand exchange with capping formate on the MOL surface to serve as the active catalytic centers. The hybrid catalyst is efficient in the organic conversion and can be readily recycled and reused.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/asia.201900391 | DOI Listing |
Chem Asian J
January 2025
Department of Chemistry, Jadavpur University, Kolkata, 700032, West Bengal, India.
Herein, we present a sustainable and atom-economical approach for the synthesis of quinazolinones via acceptorless dehydrogenative coupling (ADC) using earth-abundant Co-salt, (CoCl) as the catalyst under neat condition. This method is distinguished by its green credentials, like, solvent-free, microwave-assisted heating, cost-effective, use of renewable alcohols, and generating only H and water as byproducts. Remarkably, this protocol achieves quinazolinone synthesis without the need for external ligands, oxidants, or additional additives.
View Article and Find Full Text PDFNat Commun
January 2025
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
The advancement of an effective hydrogen liberation technology from liquid organic hydrogen carriers, particularly cycloalkanes such as cyclohexane and methylcyclohexane, holds significance in realizing a hydrogen-centric society. However, the attainment of homogeneous catalytic acceptorless dehydrogenation characterized by elevated selectivity for thorough aromatization under mild conditions remains unrealized. In this study, a catalyst system, facilitated by a double hydrogen atom transfer processes, has been devised for the catalytic acceptorless dehydrogenation of inert cycloalkanes at ambient temperature under visible light irradiation.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
Compounds containing quaternary stereocentres are a valuable motif in biologically active compounds. Herein we present our strategy to utilise the hydrogen borrowing manifold to access α-quaternary ketones via a tandem acceptorless dehydrogenation-cyclisation cascade. This new application of the methodology results in the formation of five- and six-membered carbocycles with a high degree of diastereoselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Dalian University of Technology, Dalian 116024, China.
We report the first example of photocatalytic acceptorless dehydrogenation using cationic Eosin Y as a bifunctional photocatalyst, without metal catalysts or HAT reagents. Under Bayesian optimized conditions, a wide range of flavones were synthesized in moderate to excellent yields, many of which were reported with biological activities. Mechanistic studies suggest that flavones likely form through two HAT processes, with hydrogen release occurring photoredox.
View Article and Find Full Text PDFJ Org Chem
January 2025
Centre for Organometallic Chemistry, School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India.
A streamlined strategy for the one-pot synthesis of isoxazolone analogues has been developed through an acceptorless dehydrogenative annulation (ADA) pathway by employing new Ru(II) hydride complexes as effective catalysts. New Ru(II) complexes () tailored with N̂O chelating carbazolone benzhydrazone ligands were synthesized and their formation was confirmed using analytical and spectral techniques including FT-IR and NMR. The structural configuration of the complexes featuring an octahedral geometry around the Ru(II) ion was precisely determined by single-crystal X-ray diffraction analysis.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!