Taming the highly reactive oxonium ion.

Angew Chem Int Ed Engl

Department of Chemistry and the Material Science Institute, 1253 University of Oregon, Eugene, OR 97403-1253, USA.

Published: March 2009

'Onium rings: Incorporation of the trivalent oxygen atom as a structural element within the tricyclic core of 1-3 imparts unprecedented stability to this "extraordinary" class of tertiary oxonium ions. Cation 1 is the least reactive and can be refluxed in water for 72 hours with no noticeable decomposition.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.200805417DOI Listing

Publication Analysis

Top Keywords

taming highly
4
highly reactive
4
reactive oxonium
4
oxonium ion
4
ion 'onium
4
'onium rings
4
rings incorporation
4
incorporation trivalent
4
trivalent oxygen
4
oxygen atom
4

Similar Publications

Taming highly enolizable aldehydes for catalytic asymmetric C-C coupling with nucleophiles remains an elusive challenge compared to widely explored simple alkyl or aryl aldehydes. Herein, we use ThDP-dependent enzymes to realize the direct C-C coupling of highly enolizable 2-phosphonate aldehydes with in situ-generated dynamically reversible nucleophiles (acyl anions). Unlike NHC-mediated reactions that yield complex mixtures of multiple adducts, our enzymatic process selectively produces biologically active β-hydroxy phosphonates with high yields (up to 95%) and excellent enantioselectivities (up to 99% ee).

View Article and Find Full Text PDF

Tailored charge-neutral self-assembled LZn container for taming oxalate.

Beilstein J Org Chem

November 2024

Department of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.

Article Synopsis
  • Dicarboxylic acids, especially oxalate, are essential in biological processes and health, highlighting the need for effective detection methods.
  • Despite the advantages of metal-driven self-assemblies (like metallocages) for recognizing oxalate, they are underutilized compared to traditional organic receptors.
  • A new zinc(II)-based metallocontainer has been developed, demonstrating selective binding to oxalate over other dicarboxylates, showcasing the potential of modular receptor design for challenging analytes.
View Article and Find Full Text PDF

The direct utilization of carbon dioxide as an ideal one-carbon source in value-added chemical synthesis has garnered significant attention from the standpoint of global sustainability. In this regard, the photo/electrochemical reduction of CO into useful fuels and chemical feedstocks could offer a great promise for the transition to a carbon-neutral economy. However, challenges in product selectivity continue to limit the practical application of these systems.

View Article and Find Full Text PDF

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO and HClO in Dried Foods and Living Cells.

J Agric Food Chem

May 2024

Key Laboratory of Luminescence Analysis and Molecular Sensing (Southwest University), Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China.

With the booming development of food manufacturing, developing ideal analytical tools to precisely quantify food additives is highly sought after in the food science field. Herein, a new series of quinoline-derived multifunctional fluorescent probes has been synthesized. Bearing double reactive sites, these compounds display fluorescence response toward both bisulfite (HSO) and hypochlorous acid (HClO).

View Article and Find Full Text PDF

Taming 3-Oxetanyllithium Using Continuous Flow Technology.

Org Lett

April 2024

FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, 70125, Bari, Italy.

The oxetane ring has evolved as a useful bioisostere for dimethyl and carbonyl groups for the improvement of physiochemical properties of drug candidates. Herein, we report the generation and utilization of highly unstable 3-oxetanyllithium as a hitherto unexplored nucleophile leveraging flash technology. A range of different electrophiles are suitable reaction partners in this protocol, and we demonstrate the utility of this protocol in late-stage pharmaceutical analogue synthesis.

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!