767-78-2Relevant articles and documents
Deuterium Exchange between Arenes and Deuterated Solvents in the Absence of a Transition Metal: Synthesis of D-Labeled Fluoroarenes
Salamanca, Vanesa,Albéniz, Ana C.
supporting information, p. 3206 - 3212 (2020/04/15)
Fluoroarenes can be selectively deuterated by H/D exchange with common deuterated solvents in the presence of a catalytic amount of an alkali metal carbonate or, for the less acidic arenes, stoichiometric quantities of potassium phosphate. This is a susta
Metal-Free sp2-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes
Chernichenko, Konstantin,Lindqvist, Markus,Kótai, Bianka,Nieger, Martin,Sorochkina, Kristina,Pápai, Imre,Repo, Timo
, p. 4860 - 4868 (2016/05/10)
C-H borylation is a powerful and atom-efficient method for converting affordable and abundant chemicals into versatile organic reagents used in the production of fine chemicals and functional materials. Herein we report a facile C-H borylation of aromatic and olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the sp2-C-H bond and intramolecular protonation of the sp2-C-B bond in 2-ammoniophenyl(aryl)- or -(alkenyl)borates. This common reactivity pattern serves as a platform for various catalytic reactions such as C-H borylation and hydrogenation of alkynes. In particular, we demonstrate that simple 2-aminopyridinium salts efficiently catalyze the C-H borylation of hetarenes with catecholborane. This reaction is presumably mediated by a borenium species isoelectronic to 2-aminophenylboranes.
Polyfluoroorganoboron-oxygen compounds. 2 [1]: Base-catalysed hydrodeboration of polyfluorophenyl(dihydroxy)boranes
Frohn,Adonin,Bardin,Starichenko
, p. 2834 - 2838 (2008/10/08)
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