An efficient silver-catalyzed -selective amination and aminative dearomatization of phenols with azodicarboxylates was developed. It afforded the -aminophenols or amino cyclohexadieneones from free phenols depending on whether it has a -substituent. The reaction proceeded smoothly in water under simple and mild conditions, giving the highly selective products in good yields within a short reaction time. It also showed broad substrate scope and good functional group compatibility.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.0c03147 | DOI Listing |
J Am Chem Soc
December 2024
Department of Chemistry, University of Washington, Seattle, Washington 98195, United States.
Hydroalkylation of terminal alkynes is a powerful approach to the synthesis of disubstituted alkenes. However, its application is largely unexplored in the synthesis of α,β-unsaturated carbonyls, which are common among synthetic intermediates and biologically active molecules. The thermodynamically less stable -isomers of activated alkenes have been particularly challenging to access because of their propensity for isomerization and the paucity of reliable -selective hydroalkylation methods.
View Article and Find Full Text PDFPolymers (Basel)
November 2024
Faculty of Mathematics and Natural Sciences, Chair of Inorganic Chemistry, University of Wuppertal, Gaussstraße 20, 42119 Wuppertal, Germany.
Transitioning from crude oil to renewable sources of carbon-based chemicals is critical for advancing sustainable development. Lignin, a wood-derived biomacromolecule, holds great potential as a renewable feedstock, but efficient depolymerization and dearomatization methods are required to fully unlock its potential. In this investigation, we present a silver-catalyzed aqueous electrocatalytic method for the selective depolymerization and partial dearomatization of soda lignin under mild, ambient conditions.
View Article and Find Full Text PDFOrg Biomol Chem
November 2024
Catalysis and Fine Chemicals Division, CSIR Indian Institute of Chemical Technology, Tarnaka, Hyderabad - 500007, India.
This study introduces a silver-catalyzed method for the efficient and regioselective synthesis of pyrano heterocycles, utilizing readily available alcohols and water as nucleophiles. The method demonstrates high efficiency, delivering excellent yields and selectivity, and is scalable to gram quantities while maintaining broad functional group tolerance. Notably, the synthesized pyrano[3,4-]quinolines were successfully transformed into diverse samoquasine A derivatives, underscoring the method's applicability in natural product synthesis.
View Article and Find Full Text PDFJ Org Chem
June 2024
College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
Aromatic sulfones are the prevailing scaffolds in pharmaceutical and material sciences. However, compared to their widespread application, the selective deuterium labeling of these structures is restricted due to their electron-deficient properties. This study presents two comprehensive strategies for the deuteration of aromatic sulfones.
View Article and Find Full Text PDFJ Am Chem Soc
June 2024
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom.
Monofluoroalkenes are stable and lipophilic amide bioisosteres used in medicinal chemistry. However, efficient and stereoselective methods for synthesizing -monofluoroalkenes are underdeveloped. We envisage β-fluoro-vinyl iodonium salts (-FVIs) as coupling partners for the diverse and stereoselective synthesis of -monofluoroalkenes.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!