74866-23-2

Upstream product

• 605-02-7 1-phenylnaphthalene 
• 49610-35-7 4,4'-dibromo-1,1'-binaphthyl 
• 98-80-6 phenylboronic acid 
• 412278-55-8 4.4'-Bis-(2-N-methyl-carbamoyl-phenyl)-binaphthyl-(1.1') 
• 19259-97-3 2,2''-dimethyl-4'H,4'''H-[4',4''']bi[spiro[isoindole-1,1'-naphthalen]yl]-2,2''-dione 

Downstream Products

• 143076-97-5 3,10-diphenylperylene 

Relevant academic research and scientific papers

Reconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives

We test divalent silver sulphate, Ag(ii)SO4 as a novel reagent for oxidative coupling of aromatic hydrocarbons under ambient temperature conditions. The applicability of the C(sp2)-C(sp2) coupling protocol is illustrated for naphthalene and its 1-substituted derivatives containing either electron donating (e.g. Me, MeO, or Ph) or electron-withdrawing groups (X = F?I), leading to 4,4′-disubstituted-1,1′-binaphthyls. Coupling of 2-bromo-naphthalene yields a mixture of 2,2′-, 2,7′-, and 7,7′-dibromo-1,1′-binaphthyls together with their trimeric and tetrameric analogues. The coupling of strongly electron-withdrawing 1-CF3-naphthalene provides the 5,5′-disubstituted-1,1′-binaphthyl derivative. The new method does not require the presence of halogen substituents, in contrast to most of the known C-C coupling methods, and it preserves them, if present. Ag(ii)SO4 may be easily electrochemically regenerated from the Ag(i)HSO4 byproduct. However, the C-C coupling method currently suffers from low yields, up to 17%, and it requires further optimization.

Palladium nanoparticles in Suzuki cross-couplings: Tapping into the potential of tris-imidazolium salts for nanoparticle stabilization

Inspired by the proclivity of various palladium sources to form nanoparticles in imidazolium-based ionic liquids, we now report that tris-imidazolium salts bearing hexadecyl chains and a bridging mesitylene moiety are potent stabilizers of palladium nanoparticles efficiently prepared via a Chaudret-type hydrogenation of the bis(dibenzylideneacetone)palladium(0). The palladium nanoparticles have been isolated in pure form and characterized by 1H nuclear magnetic resonance, transmission electron microscopy, electron diffraction and dynamic light scattering. The new materials proved effective in Suzuki cross-coupling at a loading of 0.2% palladium. Thus, using a tris-imidazolium iodide-palladium material, a series of biaryl products has been prepared starting from aryl bromides and some activated chlorides. The possibility that this catalytic activity might be due to the formation of palladium N-heterocyclic carbenes has been addressed through solid state 13C NMR and the synthesis of an imidazolium analogue in which the acidic 2-H was replaced with a methyl group. Copyright

Reductive Transformations, 20 - Synthesis of n-Alkyl-Substituted Perylenes and Terrylenes via Alkali-Metal Induced Cyclization of Oligonaphthylenes

The synthesis of two novel n-alkyl- or aryl-substituted perylenes and of an n-alkylated terrylene is possible by an alkali-metal induced cyclization of the corresponding bi- or trinaphthyls.Differences in reactivity of the naphthylenes in the ring-closure

Thallium in Organic Synthesis. 58. Regiospecific Intermolecular Oxidative Dehydrodimerization of Aromatic Compounds to Biaryls Using Thallium (III) Trifluoroacetate

Treatment of a variety of aromatic substrates with thallium(III) trifluoroacetate (TTFA) in trifluoroacetic acid (TFA), or in carbon tetrachloride or acetonitrile containing boron trifluoride etherate, results in smooth, rapid, and direct regiospecific oxidative dehydrodimerization to give symmetrical biaryls in good to excellent yield.The method is particularly useful when applied to substrates in which the ring substituents are either electron donating or mildly electron withdrawing.Aromatic substrates which contain powerful electron-withdrawing groups (CN, COOR, NO2) fail to react.The reaction is postulated to proceed via (a) reaction of TTFA with the aromatic substrate and generation of the radical cation Ar+; (b) reaction of this electrophile with the aromatic substrate; (c) oxidative aromatization of the intermediate thus produced by TTFA.Biaryls can be obtained similarly by oxidation of the same substrates with either mercury(II) trifluoroacetate in TFA containing boron trifluoride, lead(IV) acetate in acetonitrile containing boron trifluoride, iron(III) chloride in methylene chloride, or cobalt(III) fluoride in TFA.Yields in the Hg(II) and Fe(III) reactions are generally inferior to those obtained with TTFA, but those obtained in the Pb(IV) and Co(III) oxidations are in many instances comparable to, or even better than, the TTFA results.The oxidations with Hg(II), Pb(IV), Fe(III), and CO(III) are also postulated to proceed via a radical cation mechanism.