6796-01-6

Upstream product

• 17876-76-5 trimethyl(2-nitrobenzyl)silane 
• 100-39-0 benzyl bromide 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 17376-04-4 2-phenethyl iodide 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 494-19-9 9,10-dihydrodibenzazepine 
• 948-65-2 2-phenyl-indole 
• 5697-85-8 2-(2-phenylethyl)aniline 

Relevant academic research and scientific papers

Application of novel coupling reaction to preparing carbon-carbon bond structured compounds

The invention relates to application of a novel coupling reaction to preparing carbon-carbon bond structured compounds and mainly provides a reaction between alkyl indium compounds and halides. The reaction between the alkyl indium compounds and the halides can produce corresponding carbon-carbon structured products. The novel coupling reaction is high in process yield, broad in functional group tolerance and good in compatibility.

Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media

An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.

Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides

The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important functional groups.

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.

Cesium carbonate-catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross-coupling reactions

A catalytic amount of cesium carbonate (10?mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus-generated alkyl indium reagents could readily undergo palladium-catalyzed cross-coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.

Titanium-imido complexes with pendant groups- Synthesis, characterization, and evaluation of their role as precatalysts for ethylene polymerization

The synthesis of several anilines (ArPGNH2) substituted in the ortho position with pendant groups (PGs, terminated by potentially coordinative arene, thienyl, furanyl, or pyridyl functionalities) was accomplished by a two- to five-st

Ozone-mediated nitration of bicumene and derivatives with nitrogen dioxide. Preferential mesolytic bond cleavage over nuclear nitration in evidence for the electron transfer nature of the kyodai-nitration of arenes

The ozone-mediated reaction of bicumene and some derivatives 1 with nitrogen dioxide in dichloromethane at low twmperatures resulted in the facile cleavage of the central C-C bond to give the corresponding benzyl nitrate and its descendants 4-6. mesolytic bond cleavage occured almost exclusively over nuclear substitution at temperatures as low as -20 deg C, especially at low concentration (2 x 10-3 mol dm-3).This result may be rationalized in terms of initial electron transfer between the aromatic substrate and nitrogen trioxide in situ to form the aromatic radical cation, which then undergoes C-C bond scission at the benzylic position.In contrast, bibenzyl 2a is simply nitrated on the aromatic ring under similar conditions, giving the expected nitration products 7 and 8a-c along with a small amount of benzaldehyde 9.Results obtained from semi-empirical calculations and cyclic voltammetry are also in accord with the electron transfer nature of the reaction.The C-Si bond fission of benzyltrimethylsilane, C-C bond fragmentation of cyclic acetals of aromatic carbonyl compounds as well as side-chain reactions of toluene and derivatives, have all previously been observed under certain conditions of the kyodai-nitration and can be understood on a similar basis as described above.The possible involment of electron transfer processes in aromatic nitration with acetyl nitrate has also been suggested.

FLUORIDE ION INDUCED REACTIONS OF ORGANOSILANES WITH ELECTROPHILES

Benzyl- 4-picolyl- and phenylallyl(trimethyl)silanes react with electrophiles in the presence of KF/18-crown-6 or silica-TBAF under mild conditions.