62680-65-3

Upstream product

• 40400-13-3 2-Iodobenzyl bromide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 62680-67-5 2,2'-Diiod-α-methyl-cis-stilben 
• 62680-66-4 2,2'-Diiod-α-methyl-trans-stilben 
• 27686-42-6 trans-bis(o-iodophenyl)ethylene 
• 129177-58-8 (Z)-1-Acetyl-3-(2-iodobenzylidene)-2-methoxy-2,3-dihydroindole 
• 129177-57-7 2-Iodobenzylidene-triphenylphosphorane 
• 819871-34-6 C₉⁽¹³⁾CH₁₁I 
• 485755-51-9 1,1-diphenyl-3-(2-dicyanomethylphenyl)propene 
• 1080649-50-8 4-[(Z)-2-(2-iodophenyl)vinyl]-2-nitrothiophene 
• 1080649-49-5 4-[(E)-2-(2-iodophenyl)vinyl]-2-nitrothiophene 
• 1080649-32-6 4-[2-(2-iodophenyl)ethyl]-2-nitrothiophene 
• 1224238-12-3 (S)-2-(2-iodostyryl)-1-[(R)-1-phenylethyl]aziridine 
• 92106-62-2 1-iodo-2-styrylbenzene 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 55084-51-0 2-(2-methylphenyl)-1-benzothiophene 

Relevant academic research and scientific papers

Short and efficient synthesis of coronene derivatives via ruthenium-catalyzed benzannulation protocol

TpRuPPh3(CH3CN)2PF6 (3 mol %) was very active in catalytic benzannulation of 1-phenyl-2-ethynylbenzenes in dichloroethane (60 °C, 36 h) to afford phenanthrene in 95% yield. This method is applicable to the synthesis of various polycyclic aromatic hydrocarbons via two- and four-fold benzannulations, including various substituted coronene derivatives (53-86% yields) using this catalyst at a moderate loading (10 mol %).

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

Phenalenannulations: Three-Point Double Annulation Reactions that Convert Benzenes into Pyrenes

3-Point annulations, or phenalenannulations, transform a benzene ring directly into a substituted pyrene by “wrapping” two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for π-extension opens access to non-symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing a -CH2Br or a -CHO group into a pyrene moiety. Depending upon the workup choices, the process can be directed towards either tin- or iodo-substituted product formation, giving complementary choices for further various cross-coupling reactions. The two-directional bis-double annulation adds two new polyaromatic extensions with a total of six new aromatic rings at a central core.

PHENACENE COMPOUND, METHOD FOR PRODUCING PHENACENE COMPOUND AND ORGANIC LIGHT EMITTING ELEMENT

PROBLEM TO BE SOLVED: To provide a phenacene compound having a high fluorescence yield. SOLUTION: The present invention provides a phenacene compound represented by formula (1), where A is a group represented by formula (2); Z1 and Z2/sup

Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is

Transition-metal-free method for the synthesis of benzo[b]thiophenes from o -halovinylbenzenes and K2S via direct SNAr-type reaction, cyclization, and dehydrogenation process

A new, highly efficient procedure for the synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide has been developed. The reaction tolerated a wide range of functionalities, and various 2-substituted benzo[b]thiophenes

Unequivocal experimental evidence for a unified lithium salt-free wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products

The true course of the lithium salt-free Wittig reaction has long been a contentious issue in organic chemistry. Herein we report an experimental effect that is common to the Wittig reactions of all of the three major phosphonium ylide classes (non-stabilized, semi-stabilized, and stabilized): there is consistently increased selectivity for cis-oxaphosphetane and its derived products (Z-alkene and erythro-β-hydroxyphosphonium salt) in reactions involving aldehydes bearing heteroatom substituents in the β-position. The effect operates with both benzaldehydes and aliphatic aldehydes and is shown not to operate in the absence of the heteroatom substituent on the aldehyde. The discovery of an effect that is common to reactions of all ylide types strongly argues for the operation of a common mechanism in all Li salt-free Wittig reactions. In addition, the results are shown to be most easily explained by the [2+2] cycloaddition mechanism proposed by Vedejs and co-workers as supplemented by Aggarwal, Harvey, and co-workers, thus providing strong confirmatory evidence in support of that mechanism. Notably, a cooperative effect of ortho-substituents in the case of semi-stabilized ylides is confirmed and is accommodated by the cycloaddition mechanism. The effect is also shown to operate in reactions of triphenylphosphine-derived ylides and has previously been observed for reactions under aqueous conditions, thus for the first time providing evidence that kinetic control is in operation in both of these cases.

Rutheniun-catalyzed cycloisomerization of o-(ethynyl)phenylalkenes to diene derivatives via skeletal rearrangement

Treatment of a series of 2′,2′-disubstituted (oethynyl)styrenes with TpRu(PPh3)(CH3CN)2PF6 (10 mol %) in benzene (80°C, 12-18 h) efficiently gave 2-alkenyl-1H-indene derivatives. This catalytic reaction represents an atypical enyne cycloisomerization with skeletal rearrangement of starting enyne, where the C=C bond is completely cleaved and inserted by the terminal alkynyl carbon. The reaction mechanism was elucidated by a series of deuterium and 13C labeling experiments, as well as by changing the substituents at the phenyl moieties. The mechanism is proposed to involve the following key steps: 5-endo-dig cyclization of ruthenium-vinylidene intermediate, a nonclassical ion formation, and the "methylenecyclopropane-trimethylenemethane" rearrangement.