Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities

Kawaai, Kazuki; Yamaguchi, T.; Yamaguchi, Eiji; Endo, Shunsuke; Tada, Norio; Ikari, Akira; Itoh, Akichika

doi:10.1021/acs.joc.7b02933

Cited by 64 publications

(27 citation statements)

References 68 publications

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“…Anthraquinones can also be used in the photocatalytic C sp 2 ‐H bond activation of acyl groups. In 2018, Kawaai and co‐workers reported the preparation of 3‐acyl‐4‐coumarin derivatives 48 by a photoinduced cascade addition of acyl radicals (generated from aldehydes 46 ) to ynoates 47 (Scheme ) . For this transformation, 2‐(tert‐butyl)anthracene‐9,10‐dione ( XV ) was used as the photocatalyst.…”

Section: Recent Applications Of Ketones In Photochemistry and Photocamentioning

confidence: 99%

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Photochemistry of Carbonyl Compounds: Application in Metal‐Free Reactions

et al. 2019

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Synthetic organic photochemistry is an efficient and environmentally friendly alternative to assemble biologically and chemically relevant scaffolds. The photon energy allows access to reactive intermediates by using a clean energy source under mild conditions. Moreover, sustainable synthesis can be achieved by using metal-free photochemistry. In this review, the photochemistry of carbonyl compounds and their application as reagents, catalysts or promoters of metal-free photochemical transformations are discussed. Fundamental aspects and reactivity of the carbonyl compounds are briefly presented in the introduction section, followed by recent applications of carbonyl compounds in photochemical reactions. The text is organized according to the role of the carbonyl compounds in the process. First, approaches in which carbonyl compounds are employed in stoichiometric or super-stoichiometric amounts (as reaction substrates or photoinitiators) are described. Thereafter, their application as photocatalysts and photosensitizers are discussed and mechanistic studies are comprehensively presented.

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Section: Recent Applications Of Ketones In Photochemistry and Photocamentioning

confidence: 99%

“… Photoredox metal‐free catalyzed synthesis of 3‐acyl‐4‐arylcoumarin derivatives 48 through acyl radical cascade addition to ynoates …”

Section: Recent Applications Of Ketones In Photochemistry and Photocamentioning

confidence: 99%

Photochemistry of Carbonyl Compounds: Application in Metal‐Free Reactions

et al. 2019

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“…Another example of photocatalytic, acyl radical alkenylation was recently reported recently by Zhu et al The authors used C2‐acyl‐substituted benzothiazolines as acyl radical precursors and 1,1‐dicyano‐1‐alkenes, in the presence of hypervalent iodine reagents to obtain β,β‐dicyanoenones in 50–80 % yield. Additionally, few examples involving acylation of alkynes, followed by subsequent cyclization, were reported …”

Section: C–c Bond: Sp2‐sp2 Disconnectionmentioning

confidence: 99%

A Retrosynthetic Approach for Photocatalysis

et al. 2020

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Visible‐light‐mediated chemical reactions have become very popular within the last 15 years. Many excellent reviews have summarized reaction principles and recent results in photochemistry and photocatalysis. However, despite their popularity photochemistry and photoredox catalysis are not regular parts of the bachelor and master curriculum of chemistry education. As a consequence, most chemists will use in synthesis planning classic retrosynthetic disconnections and only rarely consider photocatalytic steps. The aim of this article is to be a useful tool for synthetic chemists, that are interested in the synthetic aspects of photocatalysis and looking for a specific retrosynthetic disconnection. Not only are informative schemes provided but also are the availability of the catalysts and reagents as well as the functional group tolerance of the respective method briefly discussed.

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“…Furthermore, a method for the construction 3 < ‐acyl‐4‐arylcoumarin has also been achieved via photoredox catalysis using aldehydes and ynoates (Scheme ) . The reaction initiates with hydrogen abstraction from aldehydes by photoexcited anthraquinone to generate acyl radical 114 a .…”

Section: Use Of Organic Dyes For Ketone Synthesismentioning

confidence: 99%

Recent Advances in Photoredox Methods for Ketone Synthesis

2020

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Synthesis of ketones is one of the most addressed problems in organic chemistry owing to their presence in a diverse array of drugs, pharmaceuticals, natural products and photosensitizers. Many of the limitations associated with the traditional approaches enabling the synthesis of ketones like creation of high energy acylating reagents, poor functional group tolerance, pre-activation of starting materials have been largely addressed with the advent of photoredox chemistry. This review summarizes the recent advances made in the photoredox catalyzed synthesis of ketones. 2 3 4 5 6 7 8

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Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities

Cited by 64 publications

References 68 publications

Photochemistry of Carbonyl Compounds: Application in Metal‐Free Reactions

Photochemistry of Carbonyl Compounds: Application in Metal‐Free Reactions

A Retrosynthetic Approach for Photocatalysis

Recent Advances in Photoredox Methods for Ketone Synthesis

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