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Pyridyl Radical Cation for C−H Amination of Arenes
Author(s) -
Rössler Simon L.,
Jelier Benson J.,
Tripet Pascal F.,
Shemet Andrej,
Jeschke Gunnar,
Togni Antonio,
Carreira Erick M.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810261
Subject(s) - pyridinium , chemistry , reagent , adduct , amination , radical ion , photocatalysis , surface modification , cleavage (geology) , photochemistry , electron transfer , aryl , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , materials science , ion , alkyl , fracture (geology) , composite material
Electron‐transfer photocatalysis provides access to the elusive and unprecedented N ‐pyridyl radical cation from selected N‐substituted pyridinium reagents. The resulting C(sp 2 )−H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin‐trapped N ‐pyridyl radical adduct implicate SET‐triggered, pseudo‐mesolytic cleavage of the N−X pyridinium reagents mediated by visible light.