27059-47-8

Upstream product

• 538-68-1 pentylbenzene 
• 14090-22-3 butyl-dichloro-borane 
• 100-52-7 benzaldehyde 
• 583-03-9 1-Phenyl-1-pentanol 
• 1009-14-9 phenyl butyl ketone 
• 24716-09-4 2-phenylhexanoic acid 
• 693-04-9 butyl magnesium bromide 
• 109-72-8 n-butyllithium 
• 693-03-8 n-butyl magnesium bromide 

Downstream Products

• 5638-30-2 acide 3-phenyl-heptanoique 
• 344441-05-0 2-(1-Phenylpentyl)-1-cyclohexanon 
• 88834-85-9 2-Methyl-6-(1-phenylpentyl)-1-cyclohexanon 
• 88834-70-2 2,2-Dimethyl-5-phenyl-3-nonanon 
• 88834-69-9 2,4,4-Trimethyl-5-phenyl-3-nonanon 
• 6031-02-3 2-phenylhexane 
• 344445-77-8 2-(1-Phenylpentyl)-1-cyclopentanon 
• 1009-14-9 phenyl butyl ketone 
• 1384450-58-1 (1-azidopentyl)benzene 
• 33652-83-4 (S)-(-)-1-phenylpentanol 
• 19641-53-3 (R)-1-phenylpentan-1-ol 
• 41136-23-6 meso-5,6-bis-(4-hydroxy-phenyl)-decane 
• 538-68-1 pentylbenzene 
• 27911-12-2 pent-2-en-1-ylbenzene 

Relevant academic research and scientific papers

Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals

The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine-tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site-selective chlorination of sp3 C?H bonds. This process exploits the ability of protonated N-chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical-chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H-atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C?H chlorination.

Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes

A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.

Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides. This journal is

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

Iron catalyzed halogenation of benzylic aldehydes and ketones

A simple and efficient iron-catalyzed method for chlorination of aromatic carbonyl compounds is reported. By using 4-10 mol% Fe(iii) oxo acetate catalyst, prepared by solid state atmospheric oxidation of Fe(ii) acetate, in combination with triethylsilane and chlorotrimethylsilane, hydrosilylation of benzylic carbonyl compounds with subsequent chlorination is achieved within a few hours at room temperature. This new method is mild and rapid compared to the conventional two step approach involving reduction and chlorination reactions in separate stages. Development of synthetic methodology is also supplemented here by kinetic investigation of the reaction mechanism, which supports the tentative mechanisms suggested previously for similar reactions. This journal is

Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids

Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.

Allylic and allenic halide synthesis via NbCl5- and NbBr 5-mediated alkoxide rearrangements

(Chemical Equation Presented) Addition of NbCl5 or NbBr 5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metallahalo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared by nucleophilic addition, deprotonation, or reduction. Experimentally, the niobium pentahalide halogenations are rapid, afford essentially pure (E)-allylic or -allenic halides after extraction, and are applicable to a range of aliphatic and aromatic alcohols, aldehydes, and ketones. 2009 American Chemical Society.

Fluorous solvent as a new phase-screen medium between reagents and reactants in the bromination and chlorination of alcohols

(Matrix presented) A perfluorohexane layer regulates the rate of reagent transport in the bromination and chlorination of alcohols. A fluorous triphasic U-tube method is effective for lighter reagents; the thionyl chloride layer (yellow) vanishes, and the chlorides are obtained from the right top organic layer in the chlorination of alcohols.

A new method for alkylation of aromatic aldehydes using alkylboron chloride derivatives in the presence of oxygen

Reactions of aromatic aldehydes with alkylboron chloride derivatives in the presence of oxygen have been investigated. Dialkylboron chlorides react with aryl aldehydes to produce arylalkylmethanols in good to excellent yields. Under the same reaction conditions, alkylboron dichlorides lead to the formation of arylalkyl chlorides.

Chloroalkylation of aryl aldehydes using alkylboron dichlorides in the presence of oxygen

Reactions of aryl aldehydes with alkylboron dichlorides in the presence of oxygen at room temperature produces arylalkyl chlorides in good to excellent yields.