22069-96-1Relevant academic research and scientific papers
PURE ROTATIONAL SPECTRA OF 1,2- AND 1,3-BENZENE-d2 OBSERVED BY MICROWAVE FOURIER TRANSFORM SPECTROSCOPY
Oldani, M.,Widmer, R.,Grassi, G.,Bauder, A.
, p. 31 - 40 (1988)
The pure rotational spectra of 1,2- and 1,3-benzene-d2 have been measured over the 8-18 GHz range with a pulsed microwave Fourier transform spectrometer.Rotational constants have been determined from the measured transition frequencies.Structur
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.
