Photoredox/rhodium catalysis in C–H activation for the synthesis of nitrogen containing heterocycles

Kim, Hyun Jin; Fabry, David C.; Mader, Steffen; Rueping, Magnus

doi:10.1039/c9qo00206e

Cited by 31 publications

(26 citation statements)

References 68 publications

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“…Among recent examples, we highlight the method developed by Wu and co‐workers, which consists of a visible‐light promoted intramolecular cyclization of N ‐aryl‐enaminones employing dual Ir/Co catalysis (Scheme 3a) [27] . Later, Rueping and co‐workers reported a Ru/Rh dual photocatalytic intermolecular approach for the synthesis of indoles from simple anilines and alkynes (Scheme 3b) [28] . As a very important early contribution, Stephenson and co‐workers reported a visible‐light photoredox‐mediated radical reductive deiodination strategy applicable to alkyl, alkenyl, and aryl iodides.…”

Section: Recent Developments On the Photocatalytic Synthesis Of Indoles Oxindoles And Indolinesmentioning

confidence: 99%

“…[27] Later, Rueping and coworkers reported a Ru/Rh dual photocatalytic intermolecular approach for the synthesis of indoles from simple anilines and alkynes (Scheme 3b). [28] As a very important early contribution, Stephenson and co-workers reported a visible-light photoredox-mediated radical reductive deiodination strategy applicable to alkyl, alkenyl, and aryl iodides. As part of the scope investigation, the authors showed that this protocol was also capable of promoting the reductive intramolecular radical cyclization of N-propargyl and N-allyl-2-iodo-sulfonamides affording N-tosyl indoles and indolines in good yields (Scheme 4a).…”

Section: Recent Developments On the Photocatalytic Synthesis Of Indoles Oxindoles And Indolinesmentioning

confidence: 99%

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Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

Correia

Santos

Pissinati

et al. 2021

The Chemical Record

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Over the last decade, visible‐light photocatalysis has proved to be a powerful tool for the construction of N‐heterocyclic frameworks, important constituents of natural products, insecticides, pharmacologically relevant therapeutic agents and catalysts. This account highlights recent developments and established methods towards the photocatalytic cascades for preparation of different classes of N‐heterocycles, giving emphasis on our contribution to the field.

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Section: Recent Developments On the Photocatalytic Synthesis Of Indoles Oxindoles And Indolinesmentioning

confidence: 99%

Section: Recent Developments On the Photocatalytic Synthesis Of Indoles Oxindoles And Indolinesmentioning

confidence: 99%

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

Correia

Santos

Pissinati

et al. 2021

The Chemical Record

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show abstract

“…In addition, a complementary strategy towards photocatalytic C-H annulation was disclosed by Rueping et al, allowing the synthesis of N-heterocycles such as indoles and pyrroles. The targeted heterocyclic products were obtained by cyclization of acetanilides with alkyne derivatives via a direct ortho-metalation pathway ( Figure 17) [79]. Acetyl substituents acted as DG in this transformation performed under air at high temperatures.…”

Section: Review Visible-light-mediated Photocatalysis As a Sustainablmentioning

confidence: 99%

“…The targeted heterocyclic products were obtained by cyclization of acetanilides with alkyne derivatives via a direct ortho -metalation pathway ( Fig. 17 ) [ 79 ]. Acetyl substituents acted as DG in this transformation performed under air at high temperatures.…”

Section: Reviewmentioning

confidence: 99%

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

Guillemard¹,

Wencel‐Delord²

2020

Beilstein J. Org. Chem.

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While aiming at sustainable organic synthesis, over the last decade particular attention has been focused on two modern fields, C–H bond activation, and visible-light-induced photocatalysis. Couplings through C–H bond activation involve the use of non-prefunctionalized substrates that are directly converted into more complex molecules, without the need of a previous functionalization, thus considerably reduce waste generation and a number of synthetic steps. In parallel, transformations involving photoredox catalysis promote radical reactions in the absence of radical initiators. They are conducted under particularly mild conditions while using the visible light as a cheap and economic energy source. In this way, these strategies follow the requirements of environment-friendly chemistry. Regarding intrinsic advantages as well as the complementary mode of action of the two catalytic transformations previously introduced, their merging in a synergistic dual catalytic system is extremely appealing. In that perspective, the scope of this review aims to present innovative reactions combining C–H activation and visible-light induced photocatalysis.

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“…(Scheme 25). [44] This strategy shows good functional group tolerance and environmentally friendly. Initially, the neutral dimeric Rh catalyst is converted into its cationic monomeric 67 upon treatment with the silver salt, providing the five‐membered metallacycle 68 via coordination with the oxygen of the acetyl directing group.…”

Section: Photo‐catalyzed/promoted Synthesis Of Indole Derivativesmentioning

confidence: 99%

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

2020

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The use of clean and renewable light sources is increasingly common in organic synthesis due to its safety, practicality and economy. Recently, photoredox catalysis has shown great application values in organic transformations because of its advantages of environmentally friendly and abundant resources. Indoles and their derivatives (indolines, oxindoles and isatins) are the core skeletons of some important organic compounds and widely‐present in various natural products and pharmaceuticals with different biological activities. Therefore, the research on the synthesis and modification of indoles is particularly important for chemists and pharmacologists. This review summarizes the effects of photocatalysis on indole synthesis and modification in recent decades. These transformations are accomplished by using metal photocatalysts (i. e., Ir, Ru, Ni, Cu, Fe, Au, Rh, TiO2, etc.) or non‐metallic photocatalysts (i. e., Rose Bengal, Eosin Y, quinones, naphthols, N‐heterocyclic carbenes, carbazoles, pyrylium salts, etc.), or without the need of photocatalysts. The detailed mechanisms of these photo‐catalyzed/promoted organic reactions are also highlighted deeply. And we hope this review will be helpful to researchers interested in this promising field of photocatalyzed transformations.

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Photoredox/rhodium catalysis in C–H activation for the synthesis of nitrogen containing heterocycles

Abstract: The cyclization of acetanilides with alkyne derivatives has been accomplished via a rhodium catalyzed direct C–H functionalization/cyclization pathway in the presence of a photoredox catalyst.

Cited by 31 publications

References 68 publications

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

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