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

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

doi:10.1002/anie.201507641

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

Jacob Davies, Samuel G. Booth, Stephanie Essafi, Robert A W Dryfe, Daniele Leonori

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	14017-14021
Number of pages	4
Journal	Angewandte Chemie (International Edition)
Volume	54
Issue number	47
DOIs	https://doi.org/10.1002/anie.201507641
Publication status	Published - 28 Sept 2015

Access to Document

10.1002/anie.201507641Licence: CC BY

http://onlinelibrary.wiley.com/doi/10.1002/anie.201507641/abstract

Cite this

@article{9444191da7074a43ae89ee8f97cf42ca,

title = "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.",

author = "Jacob Davies and Booth, {Samuel G.} and Stephanie Essafi and Dryfe, {Robert A W} and Daniele Leonori",

note = "D.L. thanks the European Union for a Marie Curie Career Integration Grant (PCIG13-GA-2013-631556) and the School of Chemistry at the University of Manchester for generous support",

year = "2015",

month = sep,

day = "28",

doi = "10.1002/anie.201507641",

language = "English",

volume = "54",

pages = "14017--14021",

journal = "Angewandte Chemie (International Edition)",

issn = "1433-7851",

publisher = "John Wiley & Sons Ltd",

number = "47",

}

TY - JOUR

T1 - Visible Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination- and Iminohydroxylation-Cyclization Reactions

AU - Davies, Jacob

AU - Booth, Samuel G.

AU - Essafi, Stephanie

AU - Dryfe, Robert A W

AU - Leonori, Daniele

N1 - D.L. thanks the European Union for a Marie Curie Career Integration Grant (PCIG13-GA-2013-631556) and the School of Chemistry at the University of Manchester for generous support

PY - 2015/9/28

Y1 - 2015/9/28

N2 - 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.

AB - 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.

U2 - 10.1002/anie.201507641

DO - 10.1002/anie.201507641

M3 - Article

SN - 1433-7851

VL - 54

SP - 14017

EP - 14021

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 47

ER -

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

Abstract

Access to Document

Fingerprint

Cite this