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Relevant academic research and scientific papers

Cs2CO3-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Thiols with Phosphonates and Arenes

An efficient Cs2CO3-catalyzed oxidative coupling of thiols with phosphonates and arenes that uses molecular oxygen as the oxidant is described. These reactions provide not only a novel alkali metal salt catalyzed aerobic oxidation, but also an efficient approach to thiophosphates and sulfenylarenes, which are ubiquitously found in pharmaceuticals and pesticides. The reaction proceeds under simple and mild reaction conditions, tolerates a wide range of functional groups, and is applicable to the late-stage synthesis and modification of bioactive molecules.

Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles

Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.

NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions

Herein, we described the NH4I-catalyzed C–H bond chalcogenation of N-heteroaryls in the presence of a minimum amount of DMSO/H2O/acetic acid as additives (2.5/2.5/1 M equiv., respectively), under metal-free conditions. Under optimized conditions, a wide variety of sulfenyl/selenyl imidazo[1,2-α]pyridines were prepared in very good yields. Moreover, the present approach was also highly efficient for the chalcogenation of different 5-membered N-heteroaryls, e.g., indole, imidazothiazole, indazole and imidazopyrimidine derivatives.

Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal structure, DFT study and catalytic investigation of palladium and nickel complexes towards deacylative sulfenylation of active methylenes and regioselective 3-sulfenylation of indoles: Via thiouronium salt formation

A series of Ni(ii), Cu(ii), Co(ii), and Pd(ii) complexes have been synthesized with a chelating Schiff base ligand coordinated to a metal center with ONS donor atoms. The ligand and complexes are characterized by elemental analysis and spectroscopic techniques like FT-IR, 1H-NMR, and UV-Visible spectroscopy. The single crystal structure of the Pd(ii) complex is obtained by X-ray diffraction analysis and exhibits slightly distorted square planar geometry. The structure is optimized by DFT, TD-DFT calculation to elaborate the electronic structure and NBO for the charge distribution analysis of the Pd(ii) complex. The synthesized Pd(ii) and Ni(ii) complexes as catalysts have been investigated in the C-S cross-coupling of indoles and active methylenes. The metal propelled regioselective transformation afforded 3-sulfenylated indoles while β-diketones favored deacylated monosulfenyl ketones in an excellent yield via thiouronium salt formation. The Pd(ii) complex displays slightly better reactivity whereas the Ni(ii) complex is cost-efficient. The method is fast, easy to handle and cost effective in terms of high reactivity of catalysts, use of non-toxic solvents, and cheaper aryl halides and thiourea replace conventional sulfur sources, providing a practical access to organic transformations.

Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight

In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).

Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon-heteroatom bond formation

Catalytic cross-dehydrogenative coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions. For the first time, NOx+ was applied for catalytic C-S and C-N bond formation. A comprehensive scope for the C-H/S-H and C-H/N-H cross-dehydrogenative coupling was demonstrated with >60 examples. The sustainable cross-coupling conditions utilize ambient oxygen as the terminal oxidant, while water is the sole by-product.

Microwave-assisted regioselective sulfenylation of indoles under solvent- and metal-free conditions

Herein, we report a solvent- and metal-free methodology for the sulfenylation of indoles with sulfinic acids in the absence of an external catalyst under microwave irradiation. This environmentally friendly approach offered the desired products in moderate to excellent yields in only 10 min. Several functional group tolerances were monitored under the optimized conditions.

Microwave-assisted synthesis of 3-sulfenylindoles by sulfonyl hydrazides using organic ionic base-Br?nsted acid

A novel, efficient, and high-yielding method was developed for the synthesis of 3-sulfenylindoles via a DBU-based ionic liquid promoted sulfenylation of indoles using sulfonyl hydrazides as a thiol surrogate. The environmentally friendly procedure, easy operation and mild reaction conditions enable the tolerance of a wide scope of functionalities as well as high reaction efficiency. The synthetic procedure is suitable for both N-protected or unprotected indoles.

A solvent- and metal-free synthesis of 3-chacogenyl-indoles employing DMSO/I2 as an eco-friendly catalytic oxidation system

Herein, we describe a solvent- and metal-free method for the synthesis of 3-chalcogenyl-indoles from indoles and diorganyl dichalcogenides using an equivalent amount of DMSO as an oxidant, under catalysis by molecular iodine. This mild and eco-friendly ap

Synthesis of 3-sulfenylated indoles by a simple NaOH promoted sulfenylation reaction

The C-3 sulfenylation reaction of indoles has been achieved under mild reaction conditions by simply employing NaOH as promoter and thiols as thiolating reagents. This simple method allows for easy and rapid synthesis of various 3-sulfenylated indoles wit