61589-14-8Relevant articles and documents
The Origin of the Regioselectivity in the 2+2 Photochemical Cycloaddition Reactions of N-Benzoylindole with Alkenes: Trapping of 1,4-Biradical Intermediates with Hydrogen Selenide
Hastings, David J.,Weedon, Alan C.
, p. 4107 - 4110 (1991)
The 1,4-biradical species previously proposed as intermediates in the formation of cyclobutane adducts in the photochemical cycloaddition reaction between N-benzoylindole and alkenes have been trapped with hydrogen selenide.The structures of the trapped biradicals are consistent with the proposal that the first bond formed between the triplet excited state of the indole derivative and the alkenes is from the indole 2-position to that terminus of the alkene which is less able to stabilise a radical centre.This allows prediction of the reaction regiochemistry.Key Words: N-benzoylindole; photochemical cycloaddition; 1,4-biradicals; trapping.
Manganese Catalyzed Direct Amidation of Esters with Amines
Fu, Zhengqiang,Wang, Xinghua,Tao, Sheng,Bu, Qingqing,Wei, Donghui,Liu, Ning
, p. 2339 - 2358 (2021/02/03)
The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.
Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride
Zhang, Jin,Hou, Yanyan,Ma, Yangmin,Szostak, Michal
, p. 338 - 345 (2019/01/10)
A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.
