Visible‐Light‐Mediated Generation of Nitrogen‐Centered Radicals: Metal‐Free Hydroimination and Iminohydroxylation Cyclization Reactions | Zendy

Davies Jacob | Zendy; Booth Samuel G. | Zendy; Essafi Stephanie | Zendy; Dryfe Robert A. W. | Zendy; Leonori Daniele | Zendy

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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.

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