28953-15-3Relevant articles and documents
(NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies
Xie, Weilong,Yoon, Jung Hee,Chang, Sukbok
supporting information, p. 12605 - 12614 (2016/10/07)
Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.
Zinc promoted simple and convenient synthesis of carbamates: An easy access for amino group protection
Yadav,Reddy, Gondi Sudershan,Reddy, M. Muralidhar,Meshram
, p. 3259 - 3262 (2007/10/03)
Synthesis of alkyl, aryl, heterocyclic, carbohydrate and amino acid carbamates is described. The protection of the amino group in the presence of other functionality in amino acids demonstrates the importance of this method.
