Direct carbon-carbon bond formation strategy at α-position of tertiary amines by photoinduced electron transfer (PET) processes

Pandey, Ganesh; Rani, Kavita; Gingipalli, Lakshmaiah

doi:10.1016/s0040-4039(00)61203-0

Cited by 47 publications

(13 citation statements)

References 23 publications

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“…The cation was finally trapped by allyltrimethylsilane and afforded allylated derivative 523 in 70% yield (Scheme 166). 458 More recently, a Ru II complex 424 and a heterogeneous mesoporous graphitic carbon nitride (mpg-C 3 N 4 ) catalyst 459 were likewise used in the allylation of THIQs. In the latter case, weak nucleophiles, such as allylstannanes, allylsilanes, and allylboranes were employed as allylating agents.…”

Section: Allylationmentioning

confidence: 99%

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

2016

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The present review offers an overview of the current approaches for the photochemical and photocatalytic generation of reactive intermediates and their application in the formation of carbon-carbon bonds. Valuable synthetic targets are accessible, including arylation processes, formation of both carbo- and heterocycles, alpha- and beta-functionalization of carbonyls, and addition reactions onto double and triple bonds. According to the recent advancements in the field of visible/solar light catalysis, a significant part of the literature reported herein involves radical ions and radicals as key intermediates, with particular attention to the most recent examples. Synthetic application of carbenes, biradicals/radical pairs and carbocations have been also reported.

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Section: Allylationmentioning

confidence: 99%

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

2016

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“…1-Ethylpyrrolidine and allyltrimethylsilane react with dicyanonaphthalene (DCN) and light irradiation to 2-allyl-1-ethylpyrrolidine (Scheme 40). Therein, the amine is oxidized to the iminium ion and is attacked by an allyl radical generated from the silane in a separate SET/fragmentation process [114,115].…”

Section: Addition To Aliphatic Iminium Ionsmentioning

confidence: 99%

Radical Addition to Iminium Ions and Cationic Heterocycles

2014

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Carbon-centered radicals represent highly useful reactive intermediates in organic synthesis. Their nucleophilic character is reflected by fast additions to electron deficient C=X double bonds as present in iminium ions or cationic heterocycles. This review covers diverse reactions of preformed or in situ-generated cationic substrates with various types of C-radicals, including alkyl, alkoxyalkyl, trifluoromethyl, aryl, acyl, carbamoyl, and alkoxycarbonyl species. Despite its high reactivity, the strong interaction of the radical's SOMO with the LUMO of the cation frequently results in a high regioselectivity. Intra-and intermolecular processes such as the Minisci reaction, the Porta reaction, and the Knabe rearrangement will be discussed along with transition metal and photoredox catalysis or electrochemical methods to generate the odd-electron species.

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“…Thus, the main chemical reaction was deprotonation at the α‐carbon atom to yield an α‐amino radical that is in turn oxidized at the electrode to an iminium ion 16. The formation of the iminium cation from phenylpiperidine has been evidenced in previous studies 17–23. From this intermediate, a sequel of solvolysis and further oxidation reactions causes the stepwise degradation of the morpholine ring through intermediates 1–5 (the last one is the most abundant) down to the complete degradation, that is aniline 6 .…”

Section: Resultsmentioning

confidence: 79%

Analytical Determination and Electrochemical Characterization of the Oxazolidinone Antibiotic Linezolid

Merli¹,

Pretali²,

Fasani³

et al. 2011

Electroanalysis

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Linezolid belongs to a class of antibiotics known as oxazolidinones. It is receiving great attention due to its activity toward multidrugs resistant bacteria, and simple and cheap methods for the analysis of this compound in pharmaceutical preparations are required. In this work, the electrochemistry of the antibiotic linezolid was investigated and a differential pulse voltammetric method based on the oxidation of the oxazolidinonic compound at a glassy carbon electrode has been developed and optimized for its determination; LOD of 50 mg L À1 and a linearity up to 200 mg L À1 were reported. The electrochemical process was studied by using different electrochemical techniques and confirmed by HPLC-MS/MS.

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Direct carbon-carbon bond formation strategy at α-position of tertiary amines by photoinduced electron transfer (PET) processes

Cited by 47 publications

References 23 publications

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

Radical Addition to Iminium Ions and Cationic Heterocycles

Analytical Determination and Electrochemical Characterization of the Oxazolidinone Antibiotic Linezolid

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