Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 47, Pages 14017-14021Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507641
Keywords
electron transfer; hydroimination; iminohydroxylation; photoredox catalysis; visible light
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Funding
- European Union [PCIG13-GA-2013-631556]
- School of Chemistry at the University of Manchester
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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 Et3N was proposed as a key step of this process.
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