On the gif oxidation of alicyclic tertiary amines

Barton, Derek H. R.; Boivin, Jean; Gaudin, D.; Jankowski, Krzysztof

doi:10.1016/s0040-4039(00)99470-x

Cited by 16 publications

(11 citation statements)

References 4 publications

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“…The oxidation of nicotine ( 26 ) to cotinine can be affected by a number of reagents as a result of hyperconjugation from the pyrrolidine nitrogen atom’s lone pair to the neighboring C–H bond. [38–39] …”

Section: Conjugation and Hyperconjugationmentioning

confidence: 99%

“…The oxidation of nicotine (26) to cotinine can be effected by a number of reagents as a result of hyperconjugation from the pyrrolidine nitrogen atoms lone pair to the neighboring C À H bond. [38,39] Much as cyclopropanes and heteroatoms can serve as activating groups through hyperconjugation, the oxidation of unsaturated systems typically exhibits increased rates of oxidation relative to their saturated counterparts (Scheme 4). [40] An illustration of this point is that singlet oxygen readily oxidizes olefinic substrates by an ene process, but C(sp 3 ) À H bonds are relatively unreactive towards singlet oxygen.…”

Section: Conjugation and Hyperconjugationmentioning

confidence: 99%

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If CH Bonds Could Talk: Selective CH Bond Oxidation

2011

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C–H oxidation has a long history and an ongoing presence in research at the forefront of chemistry and interrelated fields. As such, numerous highly useful texts and reviews have been written on this subject. Logically, these are generally written from the perspective of the scope and limitations of the reagents employed. This minireview instead attempts to emphasize chemoselectivity imposed by the nature of the substrate. Consequently many landmark discoveries in the field of C–H oxidation are not discussed, but hopefully the perspective taken herein will allow for the more ready incorporation of C–H oxidation reactions into synthetic planning.

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Section: Conjugation and Hyperconjugationmentioning

confidence: 99%

Section: Conjugation and Hyperconjugationmentioning

confidence: 99%

If CH Bonds Could Talk: Selective CH Bond Oxidation

2011

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“…6 Traditionally, remote C–H oxidation has required either: (i) the use of a directing group to deliver the catalyst to a remote C–H site 7 or (ii) the use of a protecting group on nitrogen to attenuate the reactivity of the α-C–H bonds. 8 We hypothesized that the strong preference for α-oxidation could be overridden using a much simpler approach, namely in situ protonation of the amine nitrogen.…”

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confidence: 99%

Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C–H Sites

et al. 2016

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We report the development of an iron-catalyzed method for the selective oxyfunctionalization of C(sp3)–H bonds in aliphatic amine substrates. This transformation is highly selective for benzylic C–H bonds that are remote (i.e., at least 3-carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C–H sites that are α-to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing biologically active molecules.

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“…6 However, in contrast to the Murahashi system, the obtained yields are very low (<15%) and the oxidations do not proceed chemoselectively, providing side products of methylene oxygenation.…”

Section: Scheme 2 Early Ruthenium-catalyzed C α -H Oxidationsmentioning

confidence: 96%

Cα–H Oxidations of Amines to Amides: Expanding Mechanistic Understanding and Amine Scope through Catalyst Development

Legacy

Emmert

2016

Synlett

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This highlight provides a general overview of C α -H oxidations of amines to form amides. Initial as well as recent examples are reviewed with a particular focus on existing challenges regarding substrate scope and reaction conditions. Finally, one very recently established catalyst system is described in detail which achieves the iron-catalyzed, C α -H oxidation of amines under mild conditions.

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On the gif oxidation of alicyclic tertiary amines

Cited by 16 publications

References 4 publications

If CH Bonds Could Talk: Selective CH Bond Oxidation

If CH Bonds Could Talk: Selective CH Bond Oxidation

Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C–H Sites

Cα–H Oxidations of Amines to Amides: Expanding Mechanistic Understanding and Amine Scope through Catalyst Development

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