85157-92-2Relevant articles and documents
Preparation method of aryl ketone compound
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Paragraph 0041-0049; 0061-0066, (2022/04/16)
The invention provides a preparation method of an aryl ketone compound, and belongs to the technical field of compound synthesis. The method comprises the following steps: under the action of a silver catalyst and water, carrying out reaction on aryl alkyne with a structure as shown in a formula 1 in a solvent at 60-120 DEG C for 12-48 hours, and separating and purifying a product after the reaction is finished, so as to obtain the single aryl ketone compound with a structure as shown in a formula I, the raw materials are easy to obtain, the experimental operation is simple, the yield of the prepared single aryl ketone compound is good, and gram-scale experiments can be carried out.
Palladium-Catalyzed Dual Ligand-Enabled Alkylation of Silyl Enol Ether and Enamide under Irradiation: Scope, Mechanism, and Theoretical Elucidation of Hybrid Alkyl Pd(I)-Radical Species
Zhao, Bin,Shang, Rui,Wang, Guang-Zu,Wang, Shaohong,Chen, Hui,Fu, Yao
, p. 1334 - 1343 (2020/02/04)
We report herein that a palladium catalyst in combination with a dual phosphine ligand system catalyzes alkylation of silyl enol ether and enamide with a broad scope of tertiary, secondary, and primary alkyl bromides under mild irradiation conditions by blue light-emitting diodes. The reactions effectively deliver α-alkylated ketones and α-alkylated N-acyl ketimines, and it is difficult to prepare the latter by other methods in a stereoselective manner. The α-alkylated N-acyl ketimine products can be further subjected to chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester to deliver chiral N-acyl-protected α-arylated aliphatic amines in high enantioselectivity up to 99% ee, thus providing a method for facile synthesis of chiral α-arylated aliphatic amines, which are of importance in medicinal chemistry research. The N-acetyl ketimine product also reacted smoothly with various types of Grignard reagents to afford sterically bulky N-acetyl α-tertiary amines in high yields. Theoretical studies in combination with experimental investigation provide understanding of the reaction mechanism with respect to the dual ligand effect and the irradiation effect in the catalytic cycle. The reaction is suggested to proceed via a hybrid alkyl Pd(I)-radical species generated by inner-sphere electron transfer of phosphine-coordinated Pd(0) species with alkyl bromide. This intriguing hybrid alkyl Pd(I)-radical species is elucidated by theoretical calculation to be a triplet species coordinated by three phosphine atoms with a distorted tetrahedral geometry, and spin prohibition rather than metal-to-ligand charge transfer contributes to the kinetic stability of the hybrid alkyl Pd(I)-radical species to impede alkyl recombination to generate Pd(II) alkyl intermediate.
Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes
Kim, Hye Ryung,Yun, Jaesook
supporting information; experimental part, p. 2943 - 2945 (2011/05/04)
The copper-catalyzed addition of bis(pinacolato)diboron to internal alkynes in the presence of methanol generates alkenylboron compounds with high levels of regio- and stereoselectivities. The catalytic efficiency is increased by using monodentate phosphine ligands, especially P(p-tolyl)3 and a range of internal alkynes was borylated in good yields. The Royal Society of Chemistry.
