501680-99-5Relevant academic research and scientific papers
Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions
Purkait, Nibadita,Kervefors, Gabriella,Linde, Erika,Olofsson, Berit
supporting information, p. 11427 - 11431 (2018/08/28)
A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.
Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions
Patel, Jay P.,Li, An-Hu,Dong, Hanqing,Korlipara, Vijaya L.,Mulvihill, Mark J.
scheme or table, p. 5975 - 5977 (2010/01/18)
Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of (het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Br?nsted acid.
