Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones.

Org Lett

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710069, P.R. China.

Published: February 2021

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete -stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.0c04174DOI Listing

Publication Analysis

Top Keywords

oxidative dehydrogenation
8
aerobic oxidative
4
dehydrogenation ketones
4
ketones 14-enediones
4
14-enediones efficient
4
efficient unprecedented
4
unprecedented strategy
4
strategy synthesis
4
synthesis 14-enediones
4
14-enediones saturated
4

Similar Publications

The storage and release of energy is an economic cornerstone. In quantum dots (QDs), energy storage is mostly governed by their surfaces, in particular by surface chemistry and faceting. The impact of surface free energy (SFE) through surface faceting has already been studied in QDs.

View Article and Find Full Text PDF

Pd(OAc)-Catalyzed Approach to Phenanthridin-6(5)-one Skeletons.

Org Lett

January 2025

School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Herein, we present a Pd(OAc)/Dppp-catalyzed synthesis of 4-arylphenanthridinones from 2-bromobenzamides and iodobenzene, which undergoes successive Ullman cross-coupling, C-H activation, and oxidative coupling dehydrogenation process. The presented methods offer an adaptable and modular synthesis route for efficiently producing a wide array of valuable phenanthridiones, demonstrating exceptional compatibility with functional groups. Alternatively, a 1:1 cross-coupling reaction utilizing an intramolecular norbornene moiety as the ligand resulted in phenanthridinones through -arylation and C-H activation.

View Article and Find Full Text PDF

Chemodivergent, enantio- and regioselective couplings of alkynes, aldehydes and silanes enabled by nickel/N-heterocyclic carbene catalysis.

Sci Bull (Beijing)

December 2024

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address:

Divergent synthesis of valuable molecules through common starting materials and metal catalysis represents a longstanding challenge and a significant research goal. We here describe chemodivergent, highly enantio- and regioselective nickel-catalyzed reductive and dehydrogenative coupling reactions of alkynes, aldehydes, and silanes. A single chiral Ni-based catalyst is leveraged to directly prepare three distinct enantioenriched products (silyl-protected trisubstituted chiral allylic alcohols, oxasilacyclopentenes, and silicon-stereogenic oxasilacyclopentenes) in a single chemical operation.

View Article and Find Full Text PDF

Degradation of organophosphate flame retardants by white-rot fungi: Degradation pathways and associated toxicity.

Sci Total Environ

January 2025

Institut de Química Avançada de Catalunya (IQAC), Spanish Council for Scientific Research (CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.

The environmental persistence of organophosphate flame retardants (OPFRs) in water is becoming and environmental concern. White Rot Fungi (WRF) have proven its capability to degrade certain OPFRs such as tributyl phosphate (TBP), tris(2-butoxyethyl) phosphate (TBEP), tris(2-chloroethyl) phosphate (TCEP) and tris(2-chloroisopropyl) phosphate (TCPP). Despite this capability, there is limited knowledge about the specific pathways involved in the degradation.

View Article and Find Full Text PDF

Converting biomass-derived molecules like 5-hydroxymethylfurfural (HMF) into value-added products alongside hydrogen production using renewable energy offers significant opportunities for sustainable chemical and energy production. Yet, HMF electrooxidation requires strong alkaline conditions and membranes for efficient conversion. These harsh conditions destabilize HMF, leading to humin formation and reduced product purity, meanwhile membranes increase costs.

View Article and Find Full Text PDF

Want 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!