29374-64-9

Upstream product

• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 5390-04-5 pent-1-yn-5-ol 
• 37464-85-0 methyl 5-phenylpent-4-enoate 
• 637-50-3 1-phenylpropene 
• 100-42-5 styrene 
• 96-48-0 4-butanolide 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 17920-83-1 5-phenyl-4-pentenoic acid 
• 98078-09-2 N'-(5-hydroxy-1-phenylpentylidene)-4-methylbenzenesulfonohydrazide 
• 110-87-2 3,4-dihydro-2H-pyran 
• 100-58-3 phenylmagnesium bromide 
• 5371-52-8 2-hydroxytetrahydrofuran 

Downstream Products

• 4203-44-5 2-phenyltetrahydropyran 
• 51758-25-9 5-phenylpent-4-en-1-al 
• 37464-87-2 (5-bromopent-1-enyl)benzene 
• 10521-91-2 5-phenylpentan-1-ol 
• 1070799-24-4 C₂₃H₂₉NO₄S 
• 1315320-15-0 C₁₇H₁₇NO₂ 
• 1315320-16-1 C₂₅H₃₁N₃O₆ 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 1392108-21-2 O-(5-phenylpent-4-enyl)-N-benzoyl-N-phenylhydroxylamine 
• 15212-27-8 2-benzyltetrahydrofuran 

Relevant academic research and scientific papers

Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.

Organocatalytic, Organic Oxidant Promoted, Enamine C?H Oxidation/Cyclopropanation Reaction

Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).

Rhodium-Catalyzed Remote C(sp3)?H Borylation of Silyl Enol Ethers

A rhodium-catalyzed remote C(sp3)?H borylation of silyl enol ethers (SEEs, E/Z mixtures) by alkene isomerization and hydroboration is reported. The reaction exhibits mild reaction conditions and excellent functional-group tolerance. This method is compatible with an array of SEEs, including linear and branched SEEs derived from aldehydes and ketones, and provides direct access to a broad range of structurally diverse 1,n-borylethers in excellent regioselectivities and good yields. These compounds are precursors to various valuable chemicals, such as 1,n-diols and aminoalcohols.

Rh(I)-catalyzed ring-opening of cyclobutanols via C–C bond activation: Synthesis of cis-olefin with a remote aldehyde

A Rh(I)-catalyzed ring-opening of cyclobutanols has been developed with ring opening products bearing cis-olefin and a remote aldehyde. Various substrates bearing different substituted aryl groups, heterocyclic groups and alkyl groups were compatible with

Enantioselective Organocatalytic Enamine C?H Oxidation/Diels- Alder Reaction

α,β-unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single-electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels-Alder reaction. This enantioselective one-pot transformation represents the first example of saturated aldehydes being used in domino Diels-Alder reaction processes and demonstrates the power of this protocol for construction of stereo-defined chiral compounds and building blocks. (Figure presented.).

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

C(alkenyl)-H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis

A catalytic method to prepare highly substituted 1,3-dienes from two different alkenes is described using a directed, palladium(II)-mediated C(alkenyl)-H activation strategy. The transformation exhibits broad scope across three synthetically useful substrate classes masked with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols, and bishomoallylic amines) and tolerates internal nonconjugated alkenes, which have traditionally been a challenging class of substrates in this type of chemistry. Catalytic turnover is enabled by either MnO2 as the stoichiometric oxidant or co-catalytic Co(OAc)2 and O2 (1 atm). Experimental and computational studies were performed to elucidate the preference for C(alkenyl)-H activation over other potential pathways. As part of this effort, a structurally unique alkenylpalladium(II) dimer was isolated and characterized.

Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base

Transition-metal-free synthesis of β-alkoxy monohydroperoxides via aerobic photooxidation using an acridinium photocatalyst was developed. This method enables the synthesis of some novel hydroperoxides. The peroxide source is molecular oxygen, which is cost-effective and atomically efficient. Magnesium oxide plays an important role as a base in the catalytic system.

Regioselective Epoxidations by Cytochrome P450 3A4 Using a Theobromine Chemical Auxiliary to Predictably Produce N-Protected β- or γ-Amino Epoxides

N-Protected β- and γ-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group. (Figure presented.).

Palladium-Catalyzed Aerobic Oxidative Cyclization of Aliphatic Alkenyl Amides for the Construction of Pyrrolizidine and Indolizidine Derivatives

An efficient palladium-catalyzed aerobic oxidative cyclization has been developed to synthesize a variety of pyrrolizidine and indolizidine derivatives from simple aliphatic alkenyl amides in moderate to good yields. The reaction features the capability of accessing various N-heterocycles and the use of molecular oxygen (1 atm) as the green oxidant.