52755-39-2

Upstream product

• 100-52-7 benzaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 495-41-0 1-phenylbut-2-en-1-one 
• 107-18-6 allyl alcohol 
• 100-58-3 phenylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 13154-14-8 1-propenylmagnesium bromide 
• 123-73-9 trans-Crotonaldehyde 
• 6386-72-7 (E)-propenyl lithium 
• 135787-84-7 2-(1-Bromo-ethyl)-3-phenyl-oxirane 
• 108-86-1 bromobenzene 
• 100-59-4 phenylmagnesium chloride 
• 591-50-4 iodobenzene 
• 80735-94-0 1-Phenyl-3-buten-1-ol 

Downstream Products

• 495-41-0 1-phenylbut-2-en-1-one 
• 74608-23-4 4-methyl-N-[(2E)-1-methyl-3-phenyl-2-propen-1-yl]benzenesulfonamide 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 51765-78-7 2-methyl-4-oxo-4-phenylbutanenitrile 
• 27617-90-9 Lithiumbutyrophenon 
• 112299-31-7 2-deuterio-1-phenyl-butan-1-one 
• 495-40-9 propiophenone 
• 120869-79-6 (Z)-trimethyl((1-phenylbut-1-en-1-yl)oxy)silane 
• 938-87-4 2-methyl-1-phenyl-butan-1-one 

Relevant academic research and scientific papers

New γ-Halo-δ-lactones and δ-Hydroxy-γ-lactones with Strong Cytotoxic Activity

This paper presents the synthesis of γ-halo-δ-lactones, δ-iodo-γ-lactones and δ-hydroxy-γ-lactones from readily available organic substrates such as trans-crotonaldehyde and aryl bromides. Crystal structure analysis was carried out for lactones that were obtained in crystalline form. All halo-δ-lactones and δ-hydroxy-γ-lactones were highly cytotoxic against gastric cancer AGS cells with IC50 values in the range of 0.0006–0.0044 mM. Some lactones showed high bactericidal activity against E. coli ATCC 8739 and S. aureus ATCC 65389, which reduced the number of CFU/mL by 70–83% and 87% respectively.

Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-Added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes.

Pd-Catalyzed Tandem Isomerization/Cyclization for the Synthesis of Aromatic Oxazaheterocycles and Pyrido[3,4- b]indoles

An effient tandem process consisting of palladium-catalyzed double-bond isomerization of long-chain olefins and subsequent intramolecular cyclization promoted by B2(OH)2 for the synthesis of aromatic oxazaheterocycles is disclosed. This strategy can also provide rapid access to pyrido[3,4-b]indoles, trans-2-olefins, and eneamides bearing various functional groups with high regio- and stereoselectivity.

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.

In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids

A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).

Rhodium-Catalyzed Remote Isomerization of Alkenyl Alcohols to Ketones

We develop herein an efficient rhodium-catalyzed remote isomerization of aromatic and aliphatic alkenyl alcohols into ketones. This catalytic process, with a commercially available catalyst and ligand ([RhCl(cod)]2 and Xantphos), features high efficiency, low catalyst loading, good functional group tolerance, a broad substrate scope, and no (sub)stoichiometric additive. Preliminary mechanistic studies suggest that this transformation involves an iterative dissociative β-hydride elimination-migration insertion process.

H-*BEA Zeolite-Catalyzed Nucleophilic Substitution in Allyl Alcohols Using Sulfonamides, Amides, and Anilines

Herein, we report a novel zeolite-catalyzed nucleophilic substitution in allyl alcohols. The product yield was improved upon the addition of NaOTf (0.05 mol-percent) using the studied zeolites. The highest yields were observed using H-*BEA(Si/Al2 = 40)/NaOTf. The scope of the reaction with respect to the nucleophile was examined using 1,3-diphenylprop-2-ene-1-ol as a model substrate under optimized reaction conditions. p-Substituted aryl sulfonamides bearing electron-rich or electron-deficient substituents, alkyl sulfonamides, and heteroaryl sulfonamides undergo the amidation reaction to produce their corresponding allyl sulfonamides in good yield. Amides and anilines exhibited low activity under the optimized conditions, however, performing the reaction at 90 °C produced the target product. The scope of the allyl alcohol was investigated using p-toluenesulfonamide as the nucleophile and the reaction proceeded with a variety of allylic alcohols. To probe the practical utility of the H-*BEA-catalyzed amidation reaction, a gram-scale reaction was performed using 1.01 g (4.8 mmol) of allyl alcohol, which afforded the target product in 88 percent yield.

A Pd-Catalyzed Site-Controlled Isomerization of Terminal Olefins

An effective Pd-catalyzed isomerization of olefins with 2-PyPPh2 as the ligand is described. A wide variety of trans-2-olefins bearing various functional groups can be obtained with high regio- A nd stereoselectivity under mild reaction conditions. The ligand is crucial for the reaction.

Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.