Mechanism of Photoredox-Initiated C-C and C-N Bond Formation by Arylation of IPrAu(I)-CF 3 and IPrAu(I)-Succinimide.

Autor: Kim S; Department of Chemistry , University of California , Berkeley , California 94720 , United States., Toste FD; Department of Chemistry , University of California , Berkeley , California 94720 , United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2019 Mar 13; Vol. 141 (10), pp. 4308-4315. Date of Electronic Publication: 2019 Jan 17.
DOI: 10.1021/jacs.8b11273
Abstrakt: Herein, we report on the photoredox-initiated gold-mediated C(sp 2 )-CF 3 and C(sp 2 )-N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C-C and C-N coupling reactions. The high-valent gold(III) intermediates are accessed by virtue of photoredox catalysis through a radical chain process. In addition, the bond-forming step of the coupling reactions is the reductive elimination from cationic gold(III) intermediates, which is supported by isolation and crystallographic characterization of key Au(III) intermediates.
Databáze: MEDLINE