Nitrogen-Centered Radical Scavengers

Höfling, Sarah B.; Heinrich, Markus R.

doi:10.1055/s-0030-1258305

Cited by 12 publications

(2 citation statements)

References 55 publications

(77 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Unfortunately, the electron-deficient nature of nitrogen-centered radicals renders their application to the direct radical β-amination of unsaturated carbonyl compounds unfavorable, at least for intermolecular reactions. 9 – 11 …”

mentioning

confidence: 99%

Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical–radical coupling

Zhou

Han

et al. 2017

Chem. Sci.

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical–radical coupling

Zhou

Han

et al. 2017

Chem. Sci.

View full text Add to dashboard Cite

show abstract

“…Inspired by current research in the field of nitrogencentered radical scavengers, 19 which comprises reagents such as sulfonyl azides, 20 nitroso compounds, 21 imines, 22 azo compounds, 23 and diazirines, 24 we focused on a possible application of arenediazonium ions 25 in a radical Beckmann-type rearrangement (Scheme 1). Instead of employing cyclic ketoximes 3, which traditionally lead to ring enlargement and the formation of lactams 4, we planned to replace the cyclic oximes 3 by hydroperoxides 2 which would also be readily accessible from ketones 1, 26 and which could be reacted with arenediazonium salts 5 under reductive conditions (Scheme 1).…”

Section: Scheme 1 Classical and Radical Version Of The Beckmann Rearrmentioning

confidence: 99%

Hydrogen Peroxide and Arenediazonium Salts as Reagents for a Radical Beckmann-Type Rearrangement

Prechter¹,

Heinrich²

2011

Synthesis

Self Cite

View full text Add to dashboard Cite

The reductive ring-opening of hydroperoxides derived from cyclic ketones leads to alkyl radicals which can effectively be trapped by arenediazonium salts. This synthetic transformation yielding azo carboxylic acids or lactams, after a reductive step, can be classified as a radical version of the well-known Beckmann rearrangement. In this article, we present results on the scope, the limitations and possible applications of this new reaction type.

show abstract

Manganese-Catalyzed N–F Bond Activation for Hydroamination and Carboamination of Alkenes

et al. 2020

Org. Lett.

View full text Add to dashboard Cite

A visible-light-promoted method for generating amidyl radicals from N-fluorosulfonamides via a manganesecatalyzed N−F bond activation strategy is reported. This protocol employs a simple manganese complex, Mn 2 (CO) 10 , as the precatalyst and a cheap silane, (MeO) 3 SiH, as both the hydrogen-atom donor and the F-atom acceptor, enabling intramolecular/intermolecular hydroaminations of alkenes, two-component carboamination of alkenes, and even three-component carboamination of alkenes. A wide range of valuable aliphatic sulfonamides can be readily prepared using these practical reactions.

show abstract

Nitrogen-Centered Radical Scavengers

Cited by 12 publications

References 55 publications

Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical–radical coupling

Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical–radical coupling

Hydrogen Peroxide and Arenediazonium Salts as Reagents for a Radical Beckmann-Type Rearrangement

Manganese-Catalyzed N–F Bond Activation for Hydroamination and Carboamination of Alkenes

Contact Info

Product

Resources

About