93008-38-9

Upstream product

• 117-34-0 2,2-diphenylacetic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 103-82-2 phenylacetic acid 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 3469-00-9 methyl 2,2-diphenylacetate 

Downstream Products

• 954-21-2 N-methyldiphenylacetamide 
• 1432499-39-2 C₂₀H₂₃NO₂ 
• 1432498-76-4 C₂₁H₂₀O 
• 1432498-99-1 C₂₁H₂₀O 

Relevant academic research and scientific papers

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.

Synthesis of various acylating agents directly from carboxylic acids

A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.

One-pot transition-metal-free synthesis of weinreb amides directly from carboxylic acids

Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production. Georg Thieme Verlag KG Stuttgart · New York.

On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents

The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of α,β-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids.

Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas

Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields.

A mild, one-pot method for the conversion of carboxylic acids into the corresponding Weinreb amides

Reaction of various carboxylic acids with N,O-dimethylhydroxylamine under modified Mukaiyama amide coupling conditions affords the corresponding Weinerb amides in generally high yield.

Efficient method for preparation of N-methoxy-N-methyl amides by reaction of lactones or esters with Me2AlCl-MeONHMe·HCl

The reaction of a lactone or an ester with dimethylaluminum chloride and N, O-dimethylhydroxylamine hydrochloride provided an efficient method for preparation of N-methoxy-N-methyl amide.