Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals

Jiaqi Jia; Yee Ann Ho; Raoul F. Bülow; Magnus Rueping

doi:10.1002/chem.201802907

Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals

Jiaqi Jia, Yee Ann Ho, Raoul F. Bülow, Magnus Rueping^*

^*Corresponding author for this work

Chemistry

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

47 Scopus citations

Abstract

The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Brønsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ-lactams, with good functional group tolerance and high yields.

Original language	English (US)
Pages (from-to)	14054-14058
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	53
DOIs	https://doi.org/10.1002/chem.201802907
State	Published - Sep 20 2018

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Brønsted base
lactam derivatives
photoredox catalysis
proton-coupled electron transfer (PCET)
radical reactions
sulfonyl radical

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

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10.1002/chem.201802907

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title = "Br{\o}nsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals",

abstract = "The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Br{\o}nsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ-lactams, with good functional group tolerance and high yields.",

keywords = "Br{\o}nsted base, lactam derivatives, photoredox catalysis, proton-coupled electron transfer (PCET), radical reactions, sulfonyl radical",

author = "Jiaqi Jia and Ho, {Yee Ann} and B{\"u}low, {Raoul F.} and Magnus Rueping",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/chem.201802907",

language = "English (US)",

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T1 - Brønsted Base Assisted Photoredox Catalysis

T2 - Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals

AU - Jia, Jiaqi

AU - Ho, Yee Ann

AU - Bülow, Raoul F.

AU - Rueping, Magnus

PY - 2018/9/20

Y1 - 2018/9/20

N2 - The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Brønsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ-lactams, with good functional group tolerance and high yields.

AB - The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Brønsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ-lactams, with good functional group tolerance and high yields.

KW - Brønsted base

KW - lactam derivatives

KW - photoredox catalysis

KW - proton-coupled electron transfer (PCET)

KW - radical reactions

KW - sulfonyl radical

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U2 - 10.1002/chem.201802907

DO - 10.1002/chem.201802907

M3 - Article

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AN - SCOPUS:85052758008

SN - 0947-6539

VL - 24

SP - 14054

EP - 14058

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 53

ER -

Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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