16466-46-9

Upstream product

• 93-98-1 N-phenyl benzoyl amide 
• 126-73-8 phosphoric acid tributyl ester 
• 98-88-4 benzoyl chloride 
• 2782-40-3 N-butylbenzamide 
• 66003-76-7 Diphenyliodonium triflate 
• 100-52-7 benzaldehyde 
• 121-44-8 triethylamine 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 147428-13-5 N-phenyl-benzimidic acid-(1-methyl-allyl ester) 
• 109-65-9 1-bromo-butane 
• 1126-78-9 N-(n-butyl)aniline 
• 147428-16-8 N-crotyl-N-phenylbenzamide 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 
• 582-78-5 N-(4-methylphenyl)benzamide 

Relevant academic research and scientific papers

Preparation of alkylated compounds using the trialkylphosphate

[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N -Acylsaccharins

The use of tertiary amines as surrogates for secondary amines has prominent advantages in terms of stabilization and ease of handling. A Ni-catalyzed transamidation of N -acylsaccharins with tertiary aromatic amines is reported. By using tert -butyl hydroperoxide as the terminal oxidant, this reaction permits selective cleavage of the C(sp 3)-N bonds of unsymmetrical tertiary aromatic amines depending on the sizes of the alkyl substituents.

Transition metal-free N-arylation of secondary amides through iodonium salts as aryne precursors

By using a diaryliodonium salt as a benzyne precursor, a transition metal-free approach for N-arylation of secondary amides is developed. This novel benzyne precursor, which can be prepared easily by a one step process from an aryl iodide, shows different reactivities with previous benzyne precursors in the N-arylation reaction. Mechanistic studies confirm the involvement of benzyne species (generated in situ from the diaryliodonium salts) as key intermediates.

NBu4NI-catalyzed oxidative amidation of aldehydes with tertiary amines

An efficient oxidative coupling protocol for amide formation has been developed. Various tertiary amines and aromatic aldehydes were oxidized to their corresponding tertiary amides in moderate to good yields in the presence of a simple nBu4NI-catalyst.

A SIMPLE AND ECONOMICAL METHOD FOR THE ALKYLATION OF BENZANILIDES

A convenient and economically feasible method for the alkylation of benzanilides using tetra-n-butyl hydrogen sulphate phase transfer catalyst, powdered NaOH and anhydrous K2CO3 is described.