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Relevant academic research and scientific papers

Solid Supported Nano Structured Cu-Catalyst for Solvent/Ligand Free C2 Amination of Azoles

Ligand- and solvent-free catalytic conditions that harness a nanostructured–CuI catalyst encapsulated in TiO2 has been reported for C2-amination of azoles (benzothiazole, benzoxazole and thiazole). The reaction is highly regioselective. The catalyst is robust, inexpensive and can be recycled up to four times. This strategy was further used for the synthesis of a small molecule with anti-HIV and anti-tumor properties.

Direct amination of azoles using CuCl2 complexes of amines under mild conditions

The efficient direct amination of azoles, including benzoxazole, benzothiazole and 1-methylbenzimidazole, was accomplished in moderate to good yields using CuCl2 complexes of amines as a readily available and effective nitrogen source. The coupling reactions were performed under mild conditions: at 30-50°C within 3-6 h, in air without oxidant, additive, ligand and anhydrous conditions.

Free Radical Synthetic Protocol for Benzothiazoles via Ring Opening of Benzotriazole: A Two-step Organic Chemistry Experiment for Undergraduate and Postgraduate Students

The utility and advantages of benzotriazole methodology have been described for the practical synthesis of benzothiazoles. The two-step synthetic procedure includes nucleophilic acyl substitution followed by benzotriazole ring cleavage under the free radical condition and subsequent cyclization via elimination of molecular nitrogen (N2). This protocol requires cheap and readily available reagents, and moreover easy to handle, thus can be used to teach undergraduate and postgraduate students about the importance of benzotriazole moiety in organic synthesis, ring cleavage chemistry, cyclization reactions, and use of industrial waste in free radical reactions. Students can also learn some important and common techniques useful in organic chemistry such as monitoring of organic reaction using thin-layer chromatography and UV, microwave (MW) technique for the synthesis, and column chromatography for the product isolation and structure determination through NMR, MS, and IR spectral analysis of the pure compounds.

Room-temperature nickel-catalyzed amination of heteroaryl/aryl chlorides with Ni(II)-(σ-Aryl) complex as precatalyst

The room-temperature cross-coupling of heteroaryl and aryl chlorides with secondary cyclic amines can be effected using Ni(II)-(σ-aryl) complex as pre-catalyst. Some useful aromatic and heteroaromatic amine derivatives were readily synthesized in moderate to good yields in the presence of the Ni(II)-(σ-aryl) complex/NHC/KOtBu/toluene system.

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

Copper(ii) ions supported on functionalized graphene oxide: an organometallic nanocatalyst for oxidative amination of azolesviaC-H/C-N bond activation

Graphene oxide (GO) was chemically modified withpara-aminobenzoic acid (PABA) to immobilize copper(ii) ions on its surface and used as a nanocatalyst for the oxidative C(sp2)-H bond amination reaction. A practical method to prepare Cu2+supported onpara-aminobenzoic acid grafted on GO was reported. The prepared Cu2+@GO/PABA was characterized by FT-IR, XRD, SEM, AFM, TEM, UV-Vis, and ICP techniques. The results showed that the morphology, distribution, and loading of copper ions could be well-adjusted by grafting of PABA on GO. Moreover, just 2 mol% of Cu2+@GO-PABA could catalyze the C-H activation reaction of benzoxazole and benzothiazole with secondary amines in >94% yields. Also, the catalyst showed very good recyclability and much less leaching of the Cu into the reaction solution. The high activity of Cu2+@GO-PABA can be ascribed to the good synergistic effects of Cu2+andpara-aminobenzoic acid grafted on graphene oxide.

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

Nickel-Catalyzed Amination of (Hetero)aryl Halides Facilitated by a Catalytic Pyridinium Additive

An efficient and operationally simple Ni-catalyzed amination protocol has been developed. This methodology features a simple NiII salt, an organic base and catalytic amounts of both a pyridinium additive and Zn metal. A diverse number of (hetero)aryl halides were coupled successfully with primary and secondary alkyl amines, and anilines in good to excellent yields. Similarly, benzophenone imine gave the corresponding N-arylation product in an excellent yield.

Dioxygen-triggered oxidative cleavage of the C-S bond towards C-N bond formation

Research on the cleavage of C-C bonds has been well developed. By comparison with this, the activation of C-S bonds remains challenging. Herein, dioxygen-triggered oxidative cleavage of C-S bonds has been achieved, delivering a series of N-containing heterocyclic compounds that are frequently found in pesticides and pharmaceuticals. Additionally, the potential utility of this protocol was further demonstrated by a gram-scale experiment. Mechanistically, dioxygen plays a key role in the cleavage of C-S bonds towards C-N bond formation.

HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.