Nanoparticles (NPs) can be prepared by simple reactions and methods from a number of materials. Their small size opens up a number of applications in different fields, among which biomedicine, including: i) drug delivery, ii) biosensors, iii) bioimaging, iv) antibacterial activity. To be able to perform such tasks, NPs must be modified with a variety of functional molecules, such as drugs, targeting groups, chemical tags or antibacterial agents, and must also be prevented from aggregation. The attachment must be stable to resist during the transportation to the targeted location. Diazonium salts, which have been widely used for coupling applications and surface modification, fulfil such criteria. Moreover, they are simple to prepare and can be easily substituted with a large number of organic groups. This review describes the use of these compounds in nanomedicine with a focus on the construction of nanohybrids derived from metal, oxide and carbon-based NPs as well as viruses.
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http://dx.doi.org/10.1016/j.cis.2021.102479 | DOI Listing |
J Org Chem
January 2025
Department of Organic Chemistry, Institute of Chemistry, Federal Fluminense University─UFF, Niteroi, Rio de Janeiro 24020-141, Brazil.
Herein, we report a direct diazenylation of active methylene compounds that is environmentally friendly, cost-effective, and scalable, utilizing a heterogeneous TiO catalyst that is both accessible and recyclable. The scope of this transformation shows excellent compatibility with both electron-rich and electron-poor diazonium salts, yielding the desired products in very good yields at room temperature.
View Article and Find Full Text PDFJ Org Chem
December 2024
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent to the allyl group. A selective allylic oxidation of the coupling products was accomplished using DDQ in the presence of silica to furnish the chalcones.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
While aromatic diazonium salts are important reagents in organic synthesis, 'Diazonium ions generated from ordinary aliphatic primary amines are usually useless for preparative purposes, since they lead to a mixture of products giving not only substitution by any nucleophile present, but also elimination and rearrangements if the substrate permits.' In this work, we report that this statement is no longer valid, and it is now possible to control diazotization of aliphatic amines by utilizing isopentyl nitrite in HFIP. This transformation enabled electrophilic aromatic substitution with these highly abundant and commercially available alkyl reagents, as well as transforming them into building blocks typically employed in organic synthesis.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
A convenient and practical method has been developed for synthesizing various -aryl pyrazoles from vinyl sulfoxonium ylides and diazonium salts. When using 1,3-disubstituted vinyl sulfoxonium ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On the other hand, employing 2,3-disubstituted vinyl sulfoxonium ylides results in the formation of 1,3,4-trisubstituted pyrazoles.
View Article and Find Full Text PDFOrg Lett
November 2024
School of Chemistry, University of Hyderabad, Gachibowli 500046, Telangana, India.
Allyl amines are vital components in various biologically important molecules and play a significant role in their function. Presently, most methods are geared toward the preparation of di- and trisubstituted allyl amines, leaving a gap for the development of more versatile approaches. We herein describe an approach to yield tetrasubstituted allyl amines through palladium (Pd)-catalyzed regioselective dicarbofunctionalization of masked N-phthalimide-protected propargyl amines.
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