Visible light photoredox-catalysed intermolecular radical addition of α-halo amides to olefins

Masaki Nakajima; Quentin Lefebvre; Magnus Rueping

doi:10.1039/c4cc00753k

Visible light photoredox-catalysed intermolecular radical addition of α-halo amides to olefins

Masaki Nakajima, Quentin Lefebvre, Magnus Rueping^*

^*Corresponding author for this work

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

68 Scopus citations

Abstract

We present α-chloro amides as a new class of α-acetyl radical precursors, which undergo a tin-free, photoredox-catalysed intermolecular α-alkylation with various olefins exclusively in an anti-Markovnikov fashion. The reaction represents a reductive atom transfer radical addition (ATRA) and provides a series of alkylated amides in good yields.

Original language	English (US)
Pages (from-to)	3619-3622
Number of pages	4
Journal	CHEMICAL COMMUNICATIONS
Volume	50
Issue number	27
DOIs	https://doi.org/10.1039/c4cc00753k
State	Published - Mar 6 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Visible light photoredox-catalysed intermolecular radical addition of α-halo amides to olefins",

abstract = "We present α-chloro amides as a new class of α-acetyl radical precursors, which undergo a tin-free, photoredox-catalysed intermolecular α-alkylation with various olefins exclusively in an anti-Markovnikov fashion. The reaction represents a reductive atom transfer radical addition (ATRA) and provides a series of alkylated amides in good yields.",

author = "Masaki Nakajima and Quentin Lefebvre and Magnus Rueping",

year = "2014",

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doi = "10.1039/c4cc00753k",

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AU - Nakajima, Masaki

AU - Lefebvre, Quentin

AU - Rueping, Magnus

PY - 2014/3/6

Y1 - 2014/3/6

N2 - We present α-chloro amides as a new class of α-acetyl radical precursors, which undergo a tin-free, photoredox-catalysed intermolecular α-alkylation with various olefins exclusively in an anti-Markovnikov fashion. The reaction represents a reductive atom transfer radical addition (ATRA) and provides a series of alkylated amides in good yields.

AB - We present α-chloro amides as a new class of α-acetyl radical precursors, which undergo a tin-free, photoredox-catalysed intermolecular α-alkylation with various olefins exclusively in an anti-Markovnikov fashion. The reaction represents a reductive atom transfer radical addition (ATRA) and provides a series of alkylated amides in good yields.

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U2 - 10.1039/c4cc00753k

DO - 10.1039/c4cc00753k

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Visible light photoredox-catalysed intermolecular radical addition of α-halo amides to olefins

Abstract

ASJC Scopus subject areas

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