452962-71-9

Upstream product

• 54655-08-2 N,N-dimethyl-2-(2-phenylethynyl)aniline 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 948-65-2 2-phenyl-indole 
• 536-74-3 phenylacetylene 
• 51234-11-8 3-iodo-2-phenyl-1H-indole 
• 74-88-4 methyl iodide 
• 874770-31-7 N-cyclohexyl-N-methyl-2-(phenylethynyl)aniline 

Downstream Products

• 1175540-21-2 2-methyl-4-(1-methyl-2-phenyl-indol-3-yl)but-3-yn-2-ol 
• 6121-45-5 1-methyl-2,3-diphenyl-1H-indole 

Relevant academic research and scientific papers

Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes

An efficient and practical protocol for the Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles towards valuable 3-halobenzo[b]thiophenes is described. Structurally diverse 3-halobenzothiophenes were obtained in good to excellent yields

MANUFACTURING METHOD OF AROMATIC IODINE COMPOUND USING DISULFIDE AS CATALYST

To manufacture an aromatic iodine compound under a mild condition at low cost and high yield.SOLUTION: There is provided a manufacturing method of an aromatic iodine compound by reacting an aromatic compound and an iodination agent in a presence of a cata

New Access to Six-Membered Phosphacycle Annulated Polyaromatic Ring System

A facile Ag-catalyzed intramolecular C–P bond formation reaction from easily accessible phosphine oxides has been developed. Several new heteroatoms fused π-conjugated molecules were synthesized from this procedure with their structures confirmed by X-ray

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives

This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

The direct C-H halogenations of indoles

A novel and efficient transition metal-free C-H bond halogenation of indole derivatives has been developed. 3-Halogenated (3-Br, 3-I) indoles are highly regioselectively produced by this protocol. Simple and readily available halide salts (TBAB, KI) are employed as the halogen source. The transition metal-free and the mild conditions make this protocol very easy to handle and practical.

Cyanine-like dyes with large bond-length alternation

Herein, the synthesis and properties of alkyne-bridged carbocations, which are analogous in structure to cyanine dyes, are reported. An alkene-bridged dye, linked at the third position of the indole, was also synthesized as a reference compound. These new carbocations are stable under ambient conditions, allowing characterization by UV/Vis and NMR (1H and 13C) spectroscopies. These techniques revealed a large degree of delocalization of the positive charge, similar to a previously reported porphyrin carbocation. The linear and nonlinear optical properties are compared with cyanine dyes and triarylmethyl cations, to investigate the effects of the bond-length alternation and the overall molecular geometry. The value of Re(γ), the real part of the third-order microscopic polarizability, of -1.3×10-33 esu for the alkyne-linked cation is comparable to that of a cyanine dye of similar length. Nondegenerate two-photon absorption spectra showed that the alkene-bridged dye exhibited characteristics of cyanines, whereas the alkyne-bridged dye is reminiscent of octupolar chromophores, such as the triarylmethyl carbocation brilliant green. Such attributes were confirmed and rationalized by quantum chemical calculations. Copyright

Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization

3-Iodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1- alkynyl)anilines using I