65727-70-0

Upstream product

• 56644-04-3 (E)-1-phenyl-1,5-hexadiene 
• 764-59-0 hex-5-en-1-al 
• 100-58-3 phenylmagnesium bromide 
• 22524-25-0 1-phenylhex-5-en-1-one 
• 821-41-0 5-Hexen-1-ol 
• 76852-79-4 1-benzoyl-5-dimethylaminopentane 
• 64132-18-9 1-phenyl-6-dimethylaminohexan-1-ol 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 100-52-7 benzaldehyde 
• 872220-83-2 2-(4-methoxybenzylsulfinyl)-N-methylbenzamide 
• 872220-84-3 N-methyl-2-(4-(trifluoromethyl)benzylsulfinyl)benzamide 
• 54705-19-0 2-(benzylthio)-N-methylbenzamide 
• 101093-83-8 2-(4-methoxy-benzylsulfanyl)-benzoic acid 
• 20054-45-9 N-methyl-2-sulfanylbenzamide 

Downstream Products

• 61608-88-6 (1-chlorohex-5-en-1-yl)benzene 
• 38383-05-0 6-bromo-6-phenyl-1-hexene 
• 190730-15-5 5-Iodo-1-phenyl-6-(toluene-4-sulfonyl)-hexan-1-ol 
• 771-98-2 1-Phenylcyclohexene 
• 15232-96-9 3-phenyl-1-cyclohexene 
• 4994-16-5 4-phenylcyclohexene 
• 63779-64-6 (Z)-1-Phenylhexa-1,5-diene 
• 56644-04-3 (E)-1-phenyl-1,5-hexadiene 
• 200641-11-8 (E)-1-Phenyl-6-(toluene-4-sulfonyl)-hex-5-en-1-ol 
• 198637-36-4 (E)-6-Phenyl-undeca-5,10-dienal 
• 198637-38-6 (E)-6-Phenyl-undeca-5,10-dienenitrile 
• 38488-04-9 2-methyl-6-phenyltetrahydropyran 
• 1393380-70-5 C₁₄H₁₈O₂ 
• 65727-70-0 (R)-1-phenylhex-5-en-1-ol 

Relevant academic research and scientific papers

Enantioselective α-Arylation of Primary Alcohols under Sequential One-Pot Catalysis

Secondary benzylic alcohols and diarylmethanols are common structural motifs of biologically active and medicinally relevant compounds. Here we report their enantioselective synthesis by α-arylation of primary aliphatic and benzylic alcohols under sequential catalysis integrating a Ru-catalyzed hydrogen transfer oxidation and a Ru-catalyzed nucleophilic addition. The method can be applied to various alcohols and aryl nucleophiles tolerating a range of functional groups, including secondary alcohols, ketones, alkenes, esters, NH amides, tertiary amines, aryl halides, and heterocycles.

Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones

We report a remote functionalization strategy, which allows the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as an active chain-walking/functionalization catalyst, ultimately generating a stabilized η3-bound Ni(II) enolate as the key selectivity-controlling intermediate.

Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds

The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.

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.

Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source

The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.

Chromium-Catalyzed Linear-Selective Alkylation of Aldehydes with Alkenes

We developed a chromium-catalyzed, photochemical, and linear-selective alkylation of aldehydes with alkylzirconium species generated in situ from a wide range of alkenes and Schwartz's reagent. Photochemical homolysis of the C-Zr bond afforded alkyl radicals, which were then trapped by a chromium complex catalyst to generate the alkylchromium(III) species for polar addition to aldehydes. The reaction proceeded with high functional group tolerance at ambient temperature under visible-light irradiation.

How an early or late transition state impacts the stereoselectivity of tetrahydropyran formation by intramolecular oxa-Michael addition

The intramolecular oxa-Michael addition giving tetrahydropyrans has been examined experimentally using both acidic and basic catalysis. With acidic catalysis, the diequatorial product is exclusively obtained in a kinetically controlled reaction in all cas

Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents

Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.

Synthesis of spirocyclic orthoesters by 'anomalous' rhodium(II)-catalysed intramolecular C-H insertions

A tetrahydropyranyl acetal bearing a proximal phenyl diazoketone substituent underwent Rh(ii)-catalysed C-H insertion via an 'anomalous' C-O bond-forming, rather than C-C bond-forming, transformation, giving spirocyclic orthoesters. Density functional theory calculations with M06 show that the formation of these anomalous products involves hydride transfer to the rhodium carbene, giving an intermediate zwitterion which undergoes C-O bond formation in preference to C-C bond formation.

Asymmetric Cycloetherification by Bifunctional Organocatalyst

Attempts to obtain enantiomerically enriched tetrahydrofuran derivatives via an intramolecular oxy -Michael addition reaction of ?-hydroxyenone is discussed. Despite previous difficulties associated with the asymmetric induction of this reaction, which can proceed even without a catalyst, a highly efficient asymmetric induction was realized using a bifunctional organocatalyst derived from a cinchona alkaloid. The reaction could be extended to ζ-hydroxyenone to yield an optically active tetrahydropyran derivative with a high ee. In these reactions, it is important for the gentle acidic and basic sites in the bifunctional organocatalyst to be arranged properly within the molecular skeleton of the catalyst. The high performance asymmetric induction relied on the affinity of the catalyst for the substrate, which played an important role. A disubstituted tetrahydropyran synthesis could be effectively performed via kinetic resolution using ζ-hydroxyenone containing a secondary alcohol moiety using a chiral phosphoric acid catalyst.