Premium
Visible‐Light‐Mediated Generation of Nitrogen‐Centered Radicals: Metal‐Free Hydroimination and Iminohydroxylation Cyclization Reactions
Author(s) -
Davies Jacob,
Booth Samuel G.,
Essafi Stephanie,
Dryfe Robert A. W.,
Leonori Daniele
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507641
Subject(s) - radical , chemistry , photochemistry , electron transfer , photocatalysis , visible spectrum , reactive intermediate , acceptor , eosin y , catalysis , organic chemistry , materials science , physics , optoelectronics , condensed matter physics
The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O ‐aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible‐light‐mediated electron transfer from novel electron donor–acceptor complexes of the oximes and Et 3 N was proposed as a key step of this process.