4877-77-4

Upstream product

• 15160-49-3 3t-(2-bromo-phenyl)-2-phenyl-acrylic acid 
• 36901-75-4 (2-bromobenzyl)triphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 95-46-5 2-methylphenyl bromide 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 103-82-2 phenylacetic acid 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 60199-33-9 ortho-bromobenzenesulfonyl hydrazide 
• 2905-25-1 o-bromobenzenesulfonyl chloride 

Downstream Products

• 66374-10-5 (Z)-2-(2-phenylethenyl)benzoic acid 
• 54737-45-0 (E)-2-bromostilbene 
• 62820-81-9 (Z)-1-formyl-2-(2-phenylethenyl)benzene 
• 91388-40-8 (Z)-1-formyl-2-(2-phenylethenyl)benzene tosylhydrazone 
• 1115095-60-7 cis-trimethyl[2-(2-phenylvinyl)phenyl]silane 
• 1138-43-8 1-iodo-2-[(Z)-2-phenylethenyl]benzene 
• 1528732-74-2 (Z)-7-(2-styrylphenyl)cyclohepta-1,3,5-triene 

Relevant academic research and scientific papers

Wittig Olefination Using Phosphonium Ion-Pair Reagents Incorporating an Endogenous Base

Despite common perception, the use of strong bases in Wittig chemistry is utterly unnecessary: we report a series of novel ion-pair phosphonium carboxylate reagents which are essentially "storable ylides". These reagents are straightforwardly prepared in excellent yields, and their fluxional nature permits clean olefination of a broad range of aldehydes and even hemiacetals.

Ready approach to poly(vinyldiphenylphosphine): A novel soluble polymer for conveniently conducting Wittig reactions

The novel poly(vinyldiphenylphosphine) could be easily prepared by using the reactions of the cheap poly(vinyl chloride) with sodium phosphides. Poly(vinyldiphenylphosphine) is soluble in common solvents while its corresponding phosphine oxide is hardly soluble in the solvents. Taking advantage of this different solubility, poly(vinyldiphenylphosphine) could be used as a soluble phosphinopolymer for the Wittig reactions. The reactions could take place efficiently to produce the corresponding olefins while the isolation of the products were simple since the resulted poly(vinyldiphenylphosphine oxide) was not soluble in the solvent and could be easily removed by filtration.

Syntheses of diarylethenes by perylene-catalyzed photodesulfonylation from ethenyl sulfones

Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.

E, Z -Selectivity in the reductive cross-coupling of two benzaldehydes to stilbenes under substrate control

Unsymmetrical E- and Z-stilbenes can be synthesized from two differently substituted benzaldehydes in a MesP(TMS)Li-promoted reductive coupling sequence. Depending on the order of addition of the two coupling partners, the same olefin can be produced in either E- or Z-enriched form under identical reaction conditions. A systematic study of the correlation between the stereochemical outcome of the reaction and the substitution pattern at the two aldehydes is presented. The results can be used as guidelines to predict the product stereochemistry. This journal is

Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedl?nder Reaction

A phosphoric acid catalyzed atroposelective Friedl?nder reaction was developed in which acetylacetone and a variety of 2′-substituted 2-Aminobenzophenones were successfully employed to give optically active biaryl quinolines in good yields and with high enantioselectivities.

Air-Driven Potassium Iodide-Mediated Oxidative Photocyclization of Stilbene Derivatives

A new method has been developed for the potassium iodide-mediated oxidative photocyclization of stilbene derivatives. Compared with conventional iodine-mediated oxidative photocyclization reactions, this new method requires shorter reaction times and affords cyclized products in yields of 45-97%. This reaction proceeds with a catalytic amount of potassium iodide and works in an air-driven manner without the addition of an external scavenger. The radical-mediated oxidative photocyclization of stilbene derivatives using TEMPO was also investigated.

Enantioselective Bromo-oxycyclization of Silanol

Relying on the nucleophilicity of silanol for building up silicon-incorporated scaffold with an enantiopure tetrasubstituted carbon center remains elusive. In this report, asymmetric bromo-oxycyclization of olefinic silanol by using chiral anionic phase-transfer catalyst is described. This protocol provided a facile entry to a wide arrangement of enantiopure benzoxasilole in moderate to excellent enantioselectivities depending on the unique reactivity of bromine/N-benzyl-DABCO complex.

Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature

Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.

Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane

Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.

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.