Direct α-Arylation of α-Amino Carbonyl Compounds with Indoles Using Visible Light Photoredox Catalysis

Wang, Zhiqiang; Hu, Ming; Huang, Xiao‐Cheng; Gong, Lei; Xie, Yu; Li, Jin‐Heng

doi:10.1021/jo301691h

Cited by 160 publications

(48 citation statements)

References 49 publications

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“…In the initial report by Stephenson, the resultant electrophilic iminium ions were trapped with nitroalkanes to deliver the corresponding α-functionalized products. This strategy has proven general for a wide range of nucleophilic coupling partners including malonates, 21 cyanide, 22 trifluoromethyl anion, 22 electron-rich aromatics, 23 and phosphonates 24 in addition to tethered amines and alcohols which forge the corresponding heterocycles via intramolecular cyclization 25 (Scheme 3). …”

Section: Amine α-Functionalizationmentioning

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: Amine α-Functionalizationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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“…Photoredox catalysis has recently been emerged as a highly appealing alternative to the use of stoichiometric organic oxidants in the area of C–H functionalization. As a result, a photoredox‐catalyzed indolation of N ‐aryl‐glycine derivatives 1 was reported by the group of Li (Scheme ) . Ru(bpy) 3 Cl 2 ( PC1 ) was then used as photocatalyst with one atmosphere of oxygen as terminal oxidant to obtain the indole amino acid derivatives 23 in good yields.…”

Section: α‐C–h Functionalization At the Peptide Backbonementioning

confidence: 99%

Site‐Selective C–H Bond Activation/Functionalization of Alpha‐Amino Acids and Peptide‐Like Derivatives

Brandhofer

Mancheño

2018

Eur J Org Chem

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Amino acids and peptides play an important role in nature, as well as in organic and pharmaceutical chemistry. Therefore, the easy, straightforward and versatile access of biogenic and unnatural derivatives is still highly demanding. This micro‐review intends to provide to the reader the current state of the art on site‐selective C–H bond functionalization technology applied on α‐amino acids and peptides, focusing on the different C–H positions that can successfully be addressed to date. It is structured in two main parts implying i) the α‐C–H functionalization at the peptide backbone and ii) the modification of the side‐chain. Herein, metal‐catalyzed C–H activation, oxidative C–H functionalization, as well as light mediated approaches, are discussed considering the challenges in reactivity and selectivity. The great potential of these transformations is also depicted with the derivatization and macrocyclization of complex peptides leading to products of pharmaceutical importance.

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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.

384

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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Direct α-Arylation of α-Amino Carbonyl Compounds with Indoles Using Visible Light Photoredox Catalysis

Abstract: A general and mild method for the construction of functionalized 2-(1H-indol-3-yl)-2-amino-carbonyl compounds was achieved, which represents the first example of direct α-arylation of α-amino carbonyl compounds with indoles using the visible light photoredox catalysis strategy.

Cited by 160 publications

References 49 publications

Photoredox Catalysis in Organic Chemistry

Photoredox Catalysis in Organic Chemistry

Site‐Selective C–H Bond Activation/Functionalization of Alpha‐Amino Acids and Peptide‐Like Derivatives

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

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