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Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions.

ABSTRACT: 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.

SUBMITTER: Davies J

PROVIDER: S-EPMC4648045 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions.

Davies Jacob J Booth Samuel G SG Essafi Stephanie S Dryfe Robert A W RA Leonori Daniele D

Angewandte Chemie (International ed. in English) 20150928 47

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 ...[more]

PMID: 26412046

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