Merging visible-light photoredox and Lewis acid catalysis for the functionalization and arylation of glycine derivatives and peptides

Zhu, Shaoqun; Rueping, Magnus

doi:10.1039/c2cc36995h

Cited by 203 publications

(62 citation statements)

References 39 publications

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“…148 In this regard, catalytic protocols which utilize Lewis acids to enhance the rate of radical trapping have been reported. 149 Of particular note is a report by Yoon and co-workers demonstrating that conjugate additions of α-amino radicals can be rendered asymmetric through the use of a chiral i -BuPyBox-ligated Lewis acid catalyst (Scheme 31a).…”

Section: Photoredox Lewis Acid Catalysismentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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In recent years, photoredox catalysis has come to the forefront in organic chemistry as a powerful strategy for the activation of small molecules. In a general sense, these approaches rely on the ability of metal complexes and organic dyes to convert visible light into chemical energy by engaging in single-electron transfer with organic substrates, thereby generating reactive intermediates. In this Perspective, we highlight the unique ability of photoredox catalysis to expedite the development of completely new reaction mechanisms, with particular emphasis placed on multicatalytic strategies that enable the construction of challenging carbon–carbon and carbon–heteroatom bonds.

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Section: Photoredox Lewis Acid Catalysismentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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“…However, efforts towards expanding the scope of amines have been recently reported. Li [82] and Rueping [83] independently reported that N -arylglycine derivatives 65 are viable substrates (Scheme 16). They are presumably converted to imines 65a that are intercepted by indoles to give the Mannich-like adducts 67 .…”

Section: Reviewmentioning

confidence: 99%

The chemistry of amine radical cations produced by visible light photoredox catalysis

Hu¹,

Wang²,

Nguyen³

et al. 2013

Beilstein J. Org. Chem.

396

228

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Amine radical cations are highly useful reactive intermediates in amine synthesis. They have displayed several modes of reactivity leading to some highly sought-after synthetic intermediates including iminium ions, α-amino radicals, and distonic ions. One appealing method to access amine radical cations is through one-electron oxidation of the corresponding amines under visible light photoredox conditions. This approach and subsequent chemistries are emerging as a powerful tool in amine synthesis. This article reviews synthetic applications of amine radical cations produced by visible light photocatalysis.1977

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“…5 In their work indoles in position C2 were successfully coupled with alkyl 2-(arylamino)acetates in the presence of Lewis acidic Zn(OAc) 2 and 1 mol% [Ir(ppy) 2 bpy]PF 6 photocatalyst.…”

Section: Lewis Acid Supported Photocatalysismentioning

confidence: 99%