121497-50-5Relevant articles and documents
Polyfluoroorganoboron-oxygen compounds. 2 [1]: Base-catalysed hydrodeboration of polyfluorophenyl(dihydroxy)boranes
Frohn,Adonin,Bardin,Starichenko
, p. 2834 - 2838 (2002)
Polyfluorinated phenyl(dihydroxy)boranes C6H5-nFnB(OH)2 (n = 3 - 5) underwent hydrodeboration (formal replacement of the (dihydroxy)boryl group by hydrogen) in the presence of bases (MeOH, 33% H2O-MeO
(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.
