14670-41-8

Upstream product

• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 1009-14-9 phenyl butyl ketone 
• 587-04-2 m-Chlorobenzaldehyde 
• 672263-60-4 1-chloro-4-(pent-1-yn-1-yl)benzene 
• 72435-61-1 1-(4-chlorobenzyl)-1H-benzo[d][1,2,3]triazole 
• 89121-80-2 erythro-(1-hydroxy-1-phenyl-2-pentyl)triphenylphosphonium bromide 
• 17369-07-2 2-(butylsulfonyl)benzo[d]thiazole 

Relevant academic research and scientific papers

Stereoselective Rhodium-Catalyzed Isomerization of Stereoisomeric Mixtures of Arylalkenes

A new efficient method for the synthesis of a high ratio of E -alkenes from E / Z mixtures of alkenes with B 2pin 2in the presence of a rhodium catalyst is described. This reaction features mild reaction conditions, broad functional group tolerance, and highly great application potential.

Facile Light-Mediated Preparation of Small Polymer-Coated Palladium-Nanoparticles and Their Application as Catalysts for Alkyne Semi-Hydrogenation

A facile light-mediated preparation of small palladium nanoparticles (PdNPs) with a diameter of 1.3 nm and low dispersity by using low-priced and readily prepared photoactive polymers is presented. These polymers act as reagents for the photochemical reduction of Pd ions and they are also stabilizers for the PdNPs generated in situ. The PdNP–polymer hybrid materials prepared by this reliable approach are efficient hydrogenation catalysts that show high activity and Z-selectivity in the semi-hydrogenation of alkynes. These PdNP–catalyst hybrid materials can be readily recycled and reused up to five times.

Light Mediated Preparation of Palladium Nanoparticles as Catalysts for Alkyne cis-Semihydrogenation

A bisacylphosphine oxide photoinitiator was used for the light mediated preparation of palladium nanoparticles (PdNPs) with a small diameter of 2.8 nm. All starting materials are commercially available, and PdNP synthesis is experimentally very easy to conduct. The PdNP-hybrid material was applied as catalyst for the semihydrogenation of various internal alkynes to provide the corresponding alkenes in excellent yields (up to 99%) and Z-selectivities (Z/E ratios up to 99/1).

Wittig reaction with ion-supported Ph3P

Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding α,β-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4′-chlorophenyl)-2-propenoate and 1-(4′-chlorophenyl)-2- (4″-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate.

Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton α to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and α,β-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(β-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a- j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

A tandem Aldol-Grob reaction of ketones with aromatic aldehydes

Aromatic aldehydes react with ketones to produce (E)-1-aryl-1-alkenesvia a tandem Aldol-Grob cleavage reaction sequence. The reaction, initiated by boron trifluoride, also produces a carboxylic acid fragment.

Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones

The conditions for the title reaction were studied for the 2-benzothiazole and 2-pyridine series and for some examples in the 2-pyrimidine series.The olefin preparations were generally observed to be more efficient for 2-BT-sulfone systems.From the data of the hundred cases studied, it can be concluded that (E)-olefins are obtained: (i) from saturated BT-sulfones and aromatic aldehydes; and (ii) from benzylic BT-sulfones and branched saturated aldehydes (isobutyraldehyde, pivalaldehyde) or α,β-ethylenic or aromatic aldehydes. (Z)-olefins arise: (i) fom propargylic BT-sulfones and saturated or aromatic aldehydes; and (ii) from allylic or benzylic Pyr-sulfones and saturated aldehydes.Possible mechanisms for this new olefination procedure were examined. - heteroaromatic sulfones, organolithium derivatives, intramolecular ipso reactions, stereochemistry, elimination, olefination.