A novel one-pot synthesis of anilines from phenols was developed. Using this methodology, anilines are produced in good yield (86%) by a reaction of phenols with 2-bromo-2-methylpropionamide and NaOH in DMA via Smiles rearrangement. Phenols, which are substituted electron-withdrawing groups, are more reactive for Smiles rearrangement. Thiophenols are also converted to anilines. The process is a convenient, safe, and inexpensive method for large-scale preparation of anilines. [reaction: see text]
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol051080k | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photo-induced amidation/Smiles rearrangement of alkenes for synthesizing quaternary-carbon-containing succinyldiamides.
Org Biomol Chem
January 2025
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, P. R. China.
Succinyldiamide derivatives are important structural motifs in various natural products, pharmaceuticals, and functional materials. Herein, a novel, mild, and environmentally friendly method was developed for synthesizing functionalized succinyldiamides each containing a quaternary carbon center. This strategy was designed to involve photocatalytic decarboxylation of readily available oxalic monoamide using a non-precious metal photocatalyst, 4CzIPN, followed by a free-radical addition/Smiles rearrangement cascade reaction of -aryl--(arylsulfonyl)acrylamides.
View Article and Find Full Text PDFPhotoredox Radical Truce-Smiles Rearrangement of Sulfinyl Acrylamides with Bromodifluoroacetamides.
Org Lett
January 2025
Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, China.
We herein report a photochemical Truce-Smiles rearrangement reaction of -sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carboncentered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce-Smiles rearrangement methods involving -sulfonyl acrylamides.
View Article and Find Full Text PDFA novel ratiometric BenzoBODIPY-Based fluorescent probe for the detection and imaging of Cysteine in living cells and zebrafish models.
Talanta
December 2024
Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, China. Electronic address:
Cysteine (Cys) plays a critical role in various biological processes, including protein synthesis, cellular signaling, and antioxidant defense. However, precise detection of Cys in biological systems remains challenging due to interference from similar thiols such as homocysteine (Hcy) and glutathione (GSH). In this study, we report the synthesis and bioimaging of a novel ratio-type fluorescent probe based on the benzoBODIPY fluorophore, designed for the ratiometric detection of Cys.
View Article and Find Full Text PDFπ-Curved Blatter radicals: Blatter helicenes.
Chem Commun (Camb)
January 2025
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Poland.
Photocyclization of 8-aryloxy-3-phenylbenzo[][1,2,4]triazines leads to π-delocalized helicene radicals 1[n] ( = 5, 6, 7) containing the ring-fused 1,4-dihydro[1,2,4]triazin-4-yl as a spin source. Single crystal XRD revealed that the photocyclization to 1[n] involves a Smiles rearrangement. Radicals 1[n] were investigated by spectroscopic, electrochemical and DFT methods, while racemic helicene 1[7] was resolved and ECD spectra were recorded.
View Article and Find Full Text PDFIron-Catalyzed SO-Retaining Smiles Rearrangement through Decarboxylation.
Org Lett
December 2024
Institute of Green Chemistry and Molecular Engineering, GBRCE for Functional Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou 510006, PR China.
Radical Smiles rearrangements have emerged as powerful methodologies for constructing carbon-carbon bonds through intramolecular radical addition and fragmentation under milder conditions, with SO released as a byproduct. However, SO-retaining Smiles rearrangements, which can yield valuable alkyl sulfone derivatives, have been scarcely explored. In this study, we present an unprecedented iron-catalyzed SO-retaining Smiles rearrangement initiated by the decarboxylation of aliphatic carboxylic acids.
View Article and Find Full Text PDFWant 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!