37496-06-3Relevant articles and documents
Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride
Cheng, Hong-Gang,Pu, Maoping,Kundu, Gourab,Schoenebeck, Franziska
supporting information, p. 331 - 334 (2019/12/30)
We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.
A Novel and Chemoselective Process of N -Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material
González-González, Carlos A.,Vega, Juan Javier Mejía,Monroy, Ricardo García,González-Calderón, Davir,Corona-Becerril, David,Fuentes-Benítes, Aydeé,Mascarúa, Joaquín Tamariz,González-Romero, Carlos
, (2018/02/28)
The process of N-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselective N-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation of N-heterocycles with direct handling of alkyl halides.
Acylation of pyrroles and their free (N-H)-derivatives via palladium-catalyzed carbopalladation of nitriles
Jafarpour, Farnaz,Hazrati, Hamideh,Darvishmolla, Masoumeh
supporting information, p. 3784 - 3788 (2015/02/19)
An efficient regioselective synthesis of 2-acylpyrroles via palladium-catalyzed addition of pyrroles with benzonitriles and subsequent hydrolysis is developed. The direct acylation reaction of protected as well as (NH)-free pyrroles proceeded smoothly to