Synthesis of indol-3-yl aryl ketones through visible-light-mediated carbonylation

Zhang, Hongtao; Gu, Lijun; Huang, Xiang‐Zhong; Wang, Rui; Jin, Cheng; Li, Gan‐Peng

doi:10.1016/j.cclet.2015.10.012

Cited by 43 publications

(16 citation statements)

References 62 publications

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“…Interestingly, during the same year, another strategy was disclosed by Li and co-workers in which they synthesized indol-3-yl aryl ketones 138 from indoles 137 (Scheme ). They presumed that indole might serve as a good nucleophile to attack the intermediate acylium ion to successfully access the desired ketones. Expectedly, both meta - and para -substituted aryldiazonium salts produced higher yields than that of ortho -substituted aryldiazonium salts due to steric repulsion.…”

Section: Reductive Carbonylation (Synthesis Of Aldehydes and Ketones)mentioning

confidence: 99%

“…In addition, this process also afforded indol-3-ylnaphthyl ketones which are known to possess high affinity binding for the cannabinoid CB1 and CB2 receptors. Overall, this methodology appeared better than Li’ approach in terms of better product yields, wider substrates scope and lesser reaction time. The authors proposed that after being excited by visible light, the excited state dye EY*[EY*/EY •+ ; E 1/2 −1.60 V vs SCE] reduced an aryl sulfonyl chloride 139 [ E 1/2 = −1.3 to −0.4 V vs SCE] to aryl radical 58 .…”

Section: Reductive Carbonylation (Synthesis Of Aldehydes and Ketones)mentioning

confidence: 99%

“…-yl aryl ketones 138 from indoles 137 (Scheme 39) 66. They presumed that indole might serve as a good nucleophile to attack the intermediate acylium ion to successfully access the desired ketones.…”

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confidence: 99%

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Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Singh

Sharma

2020

J. Org. Chem.

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In the last few decades, photocatalytic radical carbonylation strategies have received considerable attention as they are becoming a formidable tool in the toolbox of organic synthesis. These carbonylation strategies involve the incorporation of a carbon monoxide into organic molecules in an atom-and step-economical manner. Mostly, these strategies rely on the generation of an acyl radical as a key intermediate, which would be created via incorporation of CO molecule to an alkyl/aryl radical. The production of alkyl/aryl radical in these methodologies required either the high-intensity lightinduced transition-metal (TM)-catalyzed systems or visible-lightinduced photocatalytic systems that would be capable of mediating single electron transfer (SET) to the C(sp 3 )-or C(sp 2 )-hybridized coupling partners. Here, in this review, the development in the field of photocatalytic carbonylation is described by compiling the literature of the last 40 years, and their reaction mechanisms have been emphatically discussed. In addition, to aid readers, we have assimilated redox potentials of photocatalysts and substrates for a better sense of spontaneity of these photoredox carbonylation reactions.

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Section: Reductive Carbonylation (Synthesis Of Aldehydes and Ketones)mentioning

confidence: 99%

Section: Reductive Carbonylation (Synthesis Of Aldehydes and Ketones)mentioning

confidence: 99%

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Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Singh

Sharma

2020

J. Org. Chem.

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“…Generally, the electron-rich arenes gave better results over electron-deficient substrates, and nitrobenzene failed to give the expected product in the current system. In 2016, Li et al further extended this strategy to the carbonylation of indoles for the preparation of various indol-3-yl aryl ketones [39]. In addition, by employing readily available arylsulfonyl chlorides as a robust source of aryl radicals, Liang, Li and co-workers achieved the same reaction under a 80 atm CO atmosphere with irradiation by green LEDs [40].…”

Section: Introductionmentioning

confidence: 99%

Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Liu

Xiao

2020

Catalysts

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Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors.

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“…In recent years, P-radicals have been widely applied to build a range of organophosphorus compounds because they are easily generated in reactions and their high activity allows them to be trapped by many unsaturated linkages such as olefins, alkynes and isonitriles . Early methods for producing P-radicals required stoichiometric amounts of a radical initiator such as AIBN, SnBu 4 , and others, which meant that the reaction was neither economic nor functional-group compatible. Recently, the use of transition-metal-catalyzed P-radical reactions effectively solved these problems, but the use of an extra equivalent of oxidizer and invariably high reaction temperature prompted us to search for more economic and facile methods of producing P-radicals.…”

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confidence: 99%

Autoxidation Photoredox Catalysis for the Synthesis of 2-Phosphinoylindoles

Wang

Yang

2018

Org. Lett.

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A new approach to the synthesis of 2-phosphinoylindoles through photoredox catalysis without external oxidants has been developed. Promoted by a ruthenium photoredox catalyst, a broad scope of 2-phosphinoylindoles can be synthesized through phosphinoylation/cyclization of diphenylphosphine oxide at room temperature under irradiation without external oxidants. The estrone skeleton isocyan is also an amenable substrate for this cyclization, yielding a molecule that has potential medicinal applications.

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Synthesis of indol-3-yl aryl ketones through visible-light-mediated carbonylation

Cited by 43 publications

References 62 publications

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Autoxidation Photoredox Catalysis for the Synthesis of 2-Phosphinoylindoles

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