Photoinduced Remote Functionalizations via Iminyl Radical- Promoted C–C and C–H Bond Cleavage Cascades

Elizabeth Dauncey; Sara Morcillo; James J.  Douglas; Nadeem S Sheikh; Daniele Leonori

doi:10.1002/anie.201710790

Photoinduced Remote Functionalizations via Iminyl Radical- Promoted C–C and C–H Bond Cleavage Cascades

Elizabeth Dauncey, Sara Morcillo, James J. Douglas, Nadeem S Sheikh, Daniele Leonori

AstraZeneca

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

Abstract

A photoinduced cascade strategy leading to a variety of differentially functionalized nitriles and ketones has been developed. These protocols rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by sp3-sp3 C-C and sp3 C-H bond cleavages gives access to distal carbon-radicals that undergo SH2-functionalizations. These mild, visible-light-mediated protocols allow remote fluorinations, chlorinations and azidations and have been applied to the modification of bioactive and structurally complex molecules.

Original language	English
Journal	Angewandte Chemie - International Edition
Early online date	8 Nov 2017
DOIs	https://doi.org/10.1002/anie.201710790
Publication status	Published - 2017

Keywords

fluorination
azidation
chlorination
remote radical functionalization cascade
photoinduced

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10.1002/anie.201710790Licence: CC BY

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title = "Photoinduced Remote Functionalizations via Iminyl Radical- Promoted C–C and C–H Bond Cleavage Cascades",

abstract = "A photoinduced cascade strategy leading to a variety of differentially functionalized nitriles and ketones has been developed. These protocols rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by sp3-sp3 C-C and sp3 C-H bond cleavages gives access to distal carbon-radicals that undergo SH2-functionalizations. These mild, visible-light-mediated protocols allow remote fluorinations, chlorinations and azidations and have been applied to the modification of bioactive and structurally complex molecules.",

keywords = "fluorination, azidation, chlorination, remote radical functionalization cascade, photoinduced",

author = "Elizabeth Dauncey and Sara Morcillo and Douglas, {James J.} and Sheikh, {Nadeem S} and Daniele Leonori",

year = "2017",

doi = "10.1002/anie.201710790",

language = "English",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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T1 - Photoinduced Remote Functionalizations via Iminyl Radical- Promoted C–C and C–H Bond Cleavage Cascades

AU - Dauncey, Elizabeth

AU - Morcillo, Sara

AU - Douglas, James J.

AU - Sheikh, Nadeem S

AU - Leonori, Daniele

PY - 2017

Y1 - 2017

N2 - A photoinduced cascade strategy leading to a variety of differentially functionalized nitriles and ketones has been developed. These protocols rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by sp3-sp3 C-C and sp3 C-H bond cleavages gives access to distal carbon-radicals that undergo SH2-functionalizations. These mild, visible-light-mediated protocols allow remote fluorinations, chlorinations and azidations and have been applied to the modification of bioactive and structurally complex molecules.

AB - A photoinduced cascade strategy leading to a variety of differentially functionalized nitriles and ketones has been developed. These protocols rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by sp3-sp3 C-C and sp3 C-H bond cleavages gives access to distal carbon-radicals that undergo SH2-functionalizations. These mild, visible-light-mediated protocols allow remote fluorinations, chlorinations and azidations and have been applied to the modification of bioactive and structurally complex molecules.

KW - fluorination

KW - azidation

KW - chlorination

KW - remote radical functionalization cascade

KW - photoinduced

U2 - 10.1002/anie.201710790

DO - 10.1002/anie.201710790

M3 - Article

SN - 1433-7851

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

ER -

Photoinduced Remote Functionalizations via Iminyl Radical- Promoted C–C and C–H Bond Cleavage Cascades

Abstract

Keywords

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