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Photocatalytic C-H Amination of Aromatics Overcoming Redox Potential Limitations.

Authors :
Morofuji T
Ikarashi G
Kano N
Source :
Organic letters [Org Lett] 2020 Apr 03; Vol. 22 (7), pp. 2822-2827. Date of Electronic Publication: 2020 Mar 24.
Publication Year :
2020

Abstract

We report the photocatalytic C-H amination of aromatics overcoming redox potential limitations. Radical cations of aromatic compounds are generated photocatalytically using Ru(phen) <subscript>3</subscript> (PF <subscript>6</subscript> ) <subscript>2</subscript> , which has a reduction potential at a high oxidation state ( E <subscript>red</subscript> (Ru <superscript>III</superscript> /Ru <superscript>II</superscript> ) = +1.37 V vs SCE) lower than the oxidation potentials of aromatic substrates ( E <subscript>ox</subscript> = +1.65 to +2.27 V vs SCE). The radical cations are trapped with pyridine to give N -arylpyridinium ions, which were converted to aromatic amines.

Details

Language :
English
ISSN :
1523-7052
Volume :
22
Issue :
7
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
32207629
Full Text :
https://doi.org/10.1021/acs.orglett.0c00822