66354-68-5

Upstream product

• 948-65-2 2-phenyl-indole 
• 333-20-0 potassium thioacyanate 
• 199277-23-1 1-azido-2-(phenylethynyl)benzene 
• 54006-72-3 3-bromo-2-phenyl-1H-indole 
• 7677-24-9 trimethylsilyl cyanide 
• 615-43-0 2-iodophenylamine 
• 98-86-2 acetophenone 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 1092497-81-8 3-allylsulfanyl-2-phenyl-1H-indole 
• 224300-36-1 bis-(2-phenyl-indol-3-yl)-disulfide 

Relevant academic research and scientific papers

Visible light-induced recyclable g-C3N4catalyzed thiocyanation of C(sp2)-H bonds in sustainable solvents

A metal-free photocatalytic strategy for the preparation of thiocyanated heterocycles from inexpensive NH4SCN has been developed using carbon nitride (g-C3N4) as a general heterogeneous catalyst in a green solvent under an

A new A3B zinc(II)-porphyrin ligand and its ruthenium(II) complex: Synthesis, photophysical properties and photocatalytic applications

Porphyrins and metalloporphyrins (or porphyrin coordination complexes) have been wildly investigated as photocatalysts in recent years. Herein we synthesized two new A3B porphyrins, a new asymmetric A3B zinc-porphyrin ligand with peripheral chelate group (pyridine dicarboxylate), and a ruthenium(II) complex of the porphyrin ligand. Their photo-physical properties were characterized and investigated by UV-Vis and fluorescent emission. The modeling of the molecular structures was optimized by DFT theoretical calculation. All porphyrin compounds exhibited strong absorbance at the Soret bands and Q bands. The free base of porphyrin possessed a higher quantum yield and a longer life time than the other two zinc-porphyrins and ruthenium-porphyrin in terms of fluorescence. Furthermore, the ruthenium-porphyrin complex can be used as a promising photocatalyst under visible light for two kinds of organic reactions: ketone-related oxidative aminothiocyanation (above 90% yield) and indole-related oxidative thiocyanation (around 80% yield) with a remarkable low amount (0.1 mmol %).

NBS-assisted palladium-catalyzed bromination/cross-coupling reaction of 2-alkynyl arylazides with KSCN: an efficient method to synthesize 3-thiocyanindoles

A novel and efficient method for the synthesis of 3-thiocyanindoles from 2-alkynyl arylazides with KSCN is described. NBS (N-bromosuccinimide) plays an important role in this cascade bromination/cross-coupling reaction. This reaction provides the 3-thiocy

Application of copper chloride dihydrate in photocatalysis of reaction of indole compound and thiocyanate compound

The invention discloses an application of copper chloride dihydrate in photocatalysis of reaction of an indole compound and a thiocyanate compound. Specifically, under the atmosphere of oxygen or air,an indole compound, an ammonium thiocyanate compound and copper chloride dihydrate are added into a reaction container provided with a stirring device, ethyl alcohol is added, a stirring reaction isconducted for 20-30 hours under room-temperature illumination, and the 3-thiocyanate indole compound is obtained. According to the method, CuCl2.2H2O is directly used as a catalyst for the first timeunder the condition of not adding any photosensitizer. Besides, the efficient preparation of the 3-thiocyanate indole compound is realized, the whole process is green, efficient and easy to operate, and the application is a good method for synthesizing the 3-thiocyanate indole compound.

Screening metal-free photocatalysts from isomorphic covalent organic frameworks for the C-3 functionalization of indoles

The visible-light-driven organic transformation using two-dimensional covalent organic frameworks (2D-COFs) as metal-free heterogeneous photocatalysts is a green and sustainable approach, and it has gained a surge of interest by virtue of the photosensitizer's high crystallinity, abundant porosity, outstanding stability, excellent light-harvesting ability and tunable structure. However, the guiding principle for designing, constructing and selecting COF-based photocatalysts has not been put forward so far. Herein, we contribute a fascinating strategy to guide the acquisition of excellent framework photocatalysts, which is to screen them from a series of isomorphic COFs. As a proof of concept, three new isomorphic pyrene-based 2D-COFs (COF-JLU23, COF-JLU24 and COF-JLU25) with variable linkers were successfully synthesized. In addition to having similar crystallinity and porosity with the same pore size and shape, their absorption, emission, bandgap, energy level, transient photocurrent response and photocatalytic activity could be easily adjustedviaconfiguring different linkers in frameworks. Indeed, COF-JLU24 with electron donor-acceptor characteristics exhibited the best photocatalytic activity among the three isomorphic COFs for C-3 functionalization reactions of indoles, even better than that of the metal-free photocatalyst g-C3N4. More importantly, the screened COF-JLU24 as a metal-free photocatalyst still displayed extensive substrate adaptability and excellent recyclability. We anticipate that this strategy will become a robust rule of thumb for fast access to COF-based photocatalysts. In addition, we still highlight that the present study broadens the applied frontier of COF-based photocatalysts.

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.

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NH4SCN and KSeCN are employed respectively as the sole reagent.

Catalyst and additive-free regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with elemental sulfur/selenium and TMSCN

A regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with TMSCN and elemental sulfur/selenium was demonstrated under catalyst-free and additive-free conditions. Dimethyl sulfoxide (DMSO) was employed as the mild oxidant as well as the solvent. The reaction is operationally simple and scalable with a broad substrate scope.

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.

Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents

A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.