The synthetic potential of thiophenols as a protic nucleophilic trigger in the transition-metal-free and Grignard-reagent-free three-component coupling involving arynes is demonstrated. Employing aldehydes as the third component, the reaction allowed the mild and broad scope synthesis of 2-arylthio benzyl alcohol derivatives in good yields. Moreover, selenophenol could be used as the nucleophilic trigger, and activated ketones could be used as the third component in this reaction.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.0c03494 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
pH-Induced Changes in the SERS Spectrum of Thiophenol at Gold Electrodes during Cyclic Voltammetry.
J Phys Chem C Nanomater Interfaces
May 2022
Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, Faculty of Science and Engineering, University of Groningen, Nijenborgh 4, Groningen 9747AG, Netherlands.
Thiophenol is a model compound used in the study of self-assembly of arylthiols on gold surfaces. In particular, changes in the surface-enhanced Raman scattering (SERS) spectra of these self-assembled monolayers (SAMs) with a change of conditions have been ascribed to, for example, differences in orientation with respect to the surface, protonation state, and electrode potential. Here, we show that potential-induced changes in the SERS spectra of SAMs of thiophenol on electrochemically roughened gold surfaces can be due to local pH changes at the electrode.
View Article and Find Full Text PDFThiophenols as Protic Nucleophilic Triggers in Aryne Three-Component Coupling.
Org Lett
November 2020
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
The synthetic potential of thiophenols as a protic nucleophilic trigger in the transition-metal-free and Grignard-reagent-free three-component coupling involving arynes is demonstrated. Employing aldehydes as the third component, the reaction allowed the mild and broad scope synthesis of 2-arylthio benzyl alcohol derivatives in good yields. Moreover, selenophenol could be used as the nucleophilic trigger, and activated ketones could be used as the third component in this reaction.
View Article and Find Full Text PDFCooperative Metal-Ligand Hydroamination Catalysis Supported by C-H Activation in Cyclam Zr(IV) Complexes.
Inorg Chem
October 2018
Centro de Química Estrutural, Instituto Superior Técnico , Universidade de Lisboa , Av. Rovisco Pais 1 , 1049-001 Lisboa , Portugal.
Complexes of the type (RCyclam)ZrCl (where R = CH═C(H)CH (All), CH═C(Me)CH (All), and PhCH (Bn)) react with suitable Grignard reagents to produce the corresponding alkyl derivatives (RCyclam)ZrR' (R' = Me, CHPh). Thermally induced double metalation of the pending arms of the cyclam ligand led to the formation of complexes ((CH═C(H)CH)Cyclam)Zr, 14, ((CH═C(Me)CH)Cyclam)Zr, 15, or ((CHCH)Cyclam)Zr, 16. These reactions proceed through C(sp)-H bond activation and R'H elimination and convert the original dianionic tetracoordinated cyclam-based ligands in tetraanionic hexacoordinated ligands that establish two new Zr-C bonds.
View Article and Find Full Text PDFElectrocatalytic proton reduction by dimeric nickel complex of a sterically demanding pincer-type NS2 aminobis(thiophenolate) ligand.
Inorg Chem
January 2015
Instituto de Química and ‡Facultad de Química, Universidad Nacional Autónoma de Mexico, Circuito Exterior, CU , Ciudad de México, DF, 04510, México.
Basic methanolysis of a sterically hindered aminobis(S-arylthiocarbamate) affords a novel aminobis(thiophenolate) pincer-type ligand NS22–; the in situ generated dianion reacts cleanly with Ni2+ and Zn2+ resulting in dimeric complexes with bridging thiophenolate ligands, as determined spectroscopically and by X-ray crystallography. The C2-symmetric [Ni(NS2)]2 dimer (1) has a square planar coordination geometry around the Ni2+ ions, while the [Zn(NS2)]2 analogue (2) is characterized by a distorted tetrahedral geometry around each independent Zn2+ ion. Addition of the neutral monodentate donor L = 2,6-xylylisocyanide to [Ni(NS2)]2 affords the monomeric complex [LNi(NS2)] (3), which is characterized in the solid state by a square planar geometry with the isocyanide donor trans to the tertiary amine of NS2.
View Article and Find Full Text PDFInP nanowires from surfactant-free thermolysis of single molecule precursors.
Dalton Trans
June 2012
Wolfson Materials and Catalysis Centre, School of Chemistry, University of East Anglia, Norwich NR4 7TJ, UK.
Indium phosphide nanofibres were grown from a single-molecule precursor, [(PhCH(2))(2)InP(SiMe(3))(2)](2), using hot injection techniques by a solution-liquid-solid (SLS) process, under "surfactant-free" conditions and without the use of protic additives. The fibres are 85-95 nm in diameter and grow from In metal droplets of 100 nm diameter. The length of the nanofibres is a function of the precursor injection temperature (rather than the growth temperature) and can be varied from 6000 nm at 210 °C to 1000 nm at 310 °C.
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!