60753-98-2

Upstream product

• 58358-45-5 p-Chlorobenzylphosphonsaeuredimethylester 
• 98-86-2 acetophenone 
• 637-87-6 1-Chloro-4-iodobenzene 
• 98-83-9 isopropenylbenzene 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 39225-17-7 diethyl 4-chlorobenzylphosphonate 
• 104-88-1 4-chlorobenzaldehyde 
• 100-42-5 styrene 
• 585-71-7 (1-bromoethyl)benzne 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 106-39-8 bromochlorobenzene 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 

Downstream Products

• 83832-35-3 1-((1S,2R)-1-Bromo-2-methoxy-2-phenyl-propyl)-4-chloro-benzene 
• 83832-19-3 1-((1R,2R)-1-Bromo-2-methoxy-2-phenyl-propyl)-4-chloro-benzene 

Relevant academic research and scientific papers

A new insight into the push-pull effect of substituents via the stilbene-like model compounds

In this paper, authors report on 1-pyridyl-2-arylethenes, 1-furyl-2-arylethylenes, 1,2-diphenylpropylenes and substituted cinnamyl anilines as stilbene-like model compounds to investigate the factors dominating the push-pull effect of substituents via usi

Synthesis of α-methylstilbenes using an aqueous Wittig methodology and application toward the development of potent human aromatase inhibitors

The development of aqueous Wittig methodology for the synthesis of α-methylstilbenes using tripropylphosphine-derived phosphonium salts is described. The Wittig olefination reaction was high yielding and allowed isolation of stilbenes by simple filtration and washing with water. The novel phosphonium salts employed were accessed via a highly efficient, regioselective addition of hydrogen bromide to styrenes. Application of the α-methylstilbenes toward the synthesis of a collection of stilbenoid-triazoles is reported and their inhibition of CYP450 19A1 (aromatase) investigated. The overall structure-activity profile provided additional evidence on the aryl halide-ketone bioisostere hypothesis and identified 6c as a potent inhibitor of aromatase in vitro (Ki = 8 nM).

Chloride-Bridged Dinuclear Rhodium(III) Complexes Bearing Chiral Diphosphine Ligands: Catalyst Precursors for Asymmetric Hydrogenation of Simple Olefins

Efficient rhodium(III) catalysts were developed for asymmetric hydrogenation of simple olefins. A new series of chloride-bridged dinuclear rhodium(III) complexes 1 were synthesized from the rhodium(I) precursor [RhCl(cod)]2, chiral diphosphine ligands, and hydrochloric acid. Complexes from the series acted as efficient catalysts for asymmetric hydrogenation of (E)-prop-1-ene-1,2-diyldibenzene and its derivatives without any directing groups, in sharp contrast to widely used rhodium(I) catalytic systems that require a directing group for high enantioselectivity. The catalytic system was applied to asymmetric hydrogenation of allylic alcohols, alkenylboranes, and unsaturated cyclic sulfones. Control experiments support the superiority of dinuclear rhodium(III) complexes 1 over typical rhodium(I) catalytic systems.

Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts

The radical carbohydroxylation of styrenes with aryldiazonium salts has been achieved under mild thermal conditions. A broad range of aryldiazonium salts was tolerated, and the reaction principle based on a radical–polar crossover mechanism could be exten

A simple, phosphine free, reusable Pd(ii)-2,2′-dihydroxybenzophenone-SBA-15 catalyst for arylation and hydrogenation reactions of alkenes

An efficient, simple, phosphine and co-catalyst free C-C coupling reaction heterogeneous catalyst via a post grafting method is developed and reported. A covalently anchored phosphine free Pd(ii) based 2,2′-dihydroxybenzophenone (DHBP) complex over organofunctionalized SBA-15 has been synthesized by the reaction between aminofunctionalized SBA-15 (NH2SBA-15) and a 2,2′-dihydroxybenzophenone (DHBP) ligand, and further complexation with Pd(ii)Cl2 to get Pd(ii)-DHBP@SBA-15. The synthesized catalysts were characterized by elemental analysis, XRD, N2 sorption analyses, TG, DTA, FT-IR, solid state 13C and 29Si NMR spectra, XPS, UV-Visible, SEM, EDAX and TEM. The synthesized catalysts were screened in arylation (Heck reactions) and hydrogenation reactions of alkenes, and the results show that Pd(ii)-DHBP@SBA-15 exhibits high conversion and selectivity towards arylation and hydrogenation reactions of alkenes with high stability. The anchored solid catalysts can be recycled effectively and reused several times without major loss in activity.

One-pot multistep synthesis of trisubstituted alkenes from N -tosylhydrazones and alcohols

A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used as starting materials. A variety of trisubstituted alkenes as well as trifluoromethyl-substituted alkenes were obtained in moderate to good yields (up to 84%) with good E-selectivity (up to 99%). Georg Thieme Verlag Stuttgart.New York.

Capture of in situ generated diazo compounds or copper carbenoids by triphenylphosphine: Selective synthesis of trans-alkenes and unsymmetric azines via reaction of aldehydes with ketone-derived N-tosylhydrazones

Copper(II) acetylacetonate-catalyzed Wittig olefination reactions of aldehydes with ketone-derived N-tosylhydrazones are reported. A series of tosylhydrazones was investigated and our results showed that the carbon number of the alkyl chain influences the E-selecivity of the alkenes greatly. Alkenes could be obtained in moderate yields and excellent E-selectivity when the carbon numbers were up to two. Under metal-free conditions, triphenylphosphine was able to capture the in situ generated diazo compounds and the corresponding unsymmetrical azines were formed in good yields.

Biopolymer-metal complex wool-Pd as a highly active heterogeneous catalyst for Heck reaction in aqueous media

Heterogeneous palladium catalysts, a biopolymer complex wool-Pd, have been applied in water-mediated coupling reactions of aryl bromides without assistance of any phosphine ligands. The catalyst was characterized by XPS, ICP. The results showed that aryl bromides could carry out the coupling reaction with a variety of alkenes at 80 °C, in aqueous media under atmospheric condition. More importantly, the cheap catalyst is stable, which shows negligible metal leaching, and retain good activity for at least ten successive runs without any additional activation treatment. This approach would be very useful from a practical viewpoint.

Phosphapalladacycle-catalyzed heck reactions for efficient synthesis of trisubstituted olefins: Evidence for palladium(0) intermediates

The coupling reaction of 1,1-disubstituted olefins (α-methyl-styrene, n-butyl methacrylate) with various aryl bromides (Heck reaction) has been studied as a new concept to synthesize trisubstituted olefins. Surprisingly, the nature of the base dramatically influences the product distribution. Thus, a systematic investigation on the role of base in Heck reactions of 1,1-disubstituted olefins was performed. Less coordinating bases like NaOAc, NaOBz or Na2CO3 yield a statistical distribution of regioisomers with the terminal olefin 10 as the major product. However, by using amines like Bu3N or diisopropylethylamine (DIPEA) as base internal olefins can be synthesized with high selectivities. With phosphapalladacycle 3 as catalyst precursor, we were able to obtain catalyst turnover numbers up to 1000, while Pd(OAc)2/2PPh3 was one order of magnitude less active. Analysis of the reaction profile by kinetic investigations led to the postulation of a reduction and subsequent oxidative addition of the catalyst precursor 3 to form 12 as catalytically active intermediate.