5203-14-5

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C11H13NO/c1-2-3-8-13-11-6-4-10(9-12)5-7-11/h4-7H,2-3,8H2,1H3

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 71-36-3 butan-1-ol 
• 109-69-3 n-Butyl chloride 
• 767-00-0 4-cyanophenol 
• 1194-02-1 4-fluorobenzonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 33863-86-4 4-(n-butyloxy)benzoyl chloride 
• 21382-98-9 p-cyanophenyl methyl sulfide 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 36800-95-0 p-cyanophenyl p-toluenesulfonate 
• 138373-10-1 4-cyanophenyl mesylate 
• 623-03-0 4-Cyanochlorobenzene 
• 619-72-7 4-nitrobenzonitrile 

Downstream Products

• 54998-33-3 4-butoxy-benzimidic acid ethyl ester; hydrochloride 
• 1498-96-0 4-butoxybenzoic acid 
• 91430-24-9 4-butoxy-benzamidoxime 
• 87578-63-0 N-(p-butoxybenzyl)formamide 
• 937725-68-3 4-butoxy-N-(4-hexyloxy-2-(propylsulfinyl)phenyl)benzamidine 
• 937725-54-7 3-(4-butoxyphenyl)-5,6,8-trifluoro-7-hexyloxy-4H-benzo[1,2,4]thiadiazine 
• 937725-60-5 C₂₃H₂₆N₂O₂SF₃ 
• 937725-51-4 3-(4-butoxyphenyl)-7-hexyloxy-4H-benzo[1,2,4]thiadiazine 
• 937725-57-0 4-butyloxy-N-(4-hexyloxyphenyl)benzamidine 
• 937725-65-0 4-butoxy-N-(2,3,5-trifluoro-4-hexyloxy-6-(propylsulfanyl)phenyl)benzamidine 
• 937725-63-8 4-butoxy-N-(4-hexyloxy-2-(propylsulfanyl)phenyl)benzamidine 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

To develop a photocatalyst with catalytical activity for substrates with low reactivities is always highly desired. Herein, based on the principle of structure–property relationships, we rationally designed the natural product cercosporin, the naturally occurring perylenequinonoid pigment, to develop a novel organic perylenephotoreductant, hexacetyl reduced cercosporin (HARCP), through structural manipulation. Compared with cercosporin, HARCP shows prominent electrochemical and photophysical characteristics with greatly improved photoreductive activity, fluorescence lifetime and fluorescence quantum yield. These properties allowed HARCP as a powerful photoreductant to efficiently realize a series of benchmark reactions, including photoreduction, alkoxylation and hydroxylation to construct C–H and C–O bonds using aryl halides as substrates under mild conditions, all of which have never been achieved by the same photocatalyst. Thus, this study well supports the notion that the principle between structural manipulation and photocatalytic activity is of great significance to design customized photocatalysts for photoredox chemistry.

Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols

The formation of aryl-alkyl ether bonds through cross coupling of alcohols with aryl halides represents a useful strategic departure from classical SN2 methods. Numerous tactics relying on Pd-, Cu-, and Ni-based catalytic systems have emerged over the past several years. Herein we disclose a Ni-catalyzed electrochemically driven protocol to achieve this useful transformation with a broad substrate scope in an operationally simple way. This electrochemical method does not require strong base, exogenous expensive transition metal catalysts (e.g., Ir, Ru), and can easily be scaled up in either a batch or flow setting. Interestingly, e-etherification exhibits an enhanced substrate scope over the mechanistically related photochemical variant as it tolerates tertiary amine functional groups in the alcohol nucleophile.

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

Preparation method of nitrile compound

The present invention belongs to the field of organic synthesis technology, specifically relates to a method for preparing a nitrile compound, aldehyde oxime derivatives as raw materials, adding DPPA and DBU, reacting in an organic solvent, one step to pr

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes

The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.

Hexaacyl reductive cercosporin photocatalyst, and preparation method and application thereof

The invention discloses a hexacyloyl reductive cercosporin photocatalyst and preparation and application thereof, belonging to the technical field of preparation methods and organic synthesis of catalysts. The preparation method comprises the following steps: adding anhydride into a mixture of cercosporin, a reducing agent and alkali, carrying out stirring at room temperature for 1-3 hours, addinganhydride, continuing reacting for 1-3 hours, and carrying out suction filtration, extraction, concentration and column chromatography purification to obtain the catalyst. The catalyst provided by the invention can catalyze reduction, coupling and other photochemical reactions of halogenated hydrocarbons, and has strong reaction activity and industrialization prospects.

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.

Nickel-catalyzed denitrative etherification of activated nitrobenzenes

Electron-deficient nitrobenzenes were coupled with phenols/alcohols to form diaryl/alkyl aryl ethers by the aid of NiCl2 as the catalyst. The reactions were conducted under ligand- and oxidant-free conditions without the exclusion of air or moisture. The initial studies upon the mechanism of the reaction revealed two solvent-dependent approaches. In molten TBAB, SNAr mechanism seems to be predominated, while, in DMF, the reaction might include the radical species.

Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides

Ni-catalyzed decarbonylative cyanation of acyl chlorides with trimethylsilyl cyanide has been achieved. This transformation is applicable to the synthesis of an array of nitrile compounds bearing a wide range of functional groups under neutral conditions. The step-by-step experimental studies revealed that the reaction sequences of the present catalytic reaction are oxidative addition, transmetalation, decarbonylation, and reductive elimination.