16466-45-8

Upstream product

• 768-52-5 N-Isopropylaniline 
• 98-88-4 benzoyl chloride 
• 10545-45-6 N-isopropyl-N-methylaniline 
• 100-52-7 benzaldehyde 
• 93-98-1 N-phenyl benzoyl amide 
• 75-26-3 isopropyl bromide 
• 513-02-0 triisopropyl phosphate 

Downstream Products

• 1596306-39-6 N-isopropyl-N-phenyl-2-((triisopropylsilyl)ethynyl)benzamide 
• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 
• 38577-69-4 N-benzyl-N-isopropylbenzenamine 

Relevant academic research and scientific papers

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).

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

Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation

A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.

Iron-catalyzed oxidative amidation of tertiary amines with aldehydes

Unconventional couple: A new oxidative coupling protocol for amide bond formation has been developed (see scheme). The method provides an efficient and practical route for the synthesis of tertiary amides from readily available tertiary amines and aldehydes in the presence of a simple FeCl2 catalyst. Mechanistic studies indicated that a peroxide and an iminium ion act as the reactive intermediates in this oxidative amidation.

EFFECT OF THE STRUCTURE OF THE AMINE ON THE RATE OF BASE-CATALYZED ACYLATION OF ALKYL AROMATIC AMINES BY BENZOYL CHLORIDE AND 2,4-DINITROPHENYL ACETATE

The kinetics of the noncatalytic and base-catalyzed aminolysis of benzoyl chloride (with pyridine as catalyst) and 2,4-dinitrophenyl acetate (with pyridine, ε-caprolactam and pyridine N-oxide as catalysts) by alkyl aromatic amines PhNHR were studied in benzene at 25 deg C.The obtained rate constants are described satisfactorily by the modified Taft equation, which takes account of the steric and inductive effects of the structure of the amine.The results are discussed in terms of base and nucleophilic mechanisms of catalysis.