The non-chain radicaloid c-alkylation of nitronate anions: further evidence for the mechanism

Katritzky, Alan R.; Chen, Jen-Luan; Marson, Charles M.; Maia, Angelamaria; Kashmiri, Muhammad Akram

doi:10.1016/s0040-4020(01)87407-x

Cited by 10 publications

(3 citation statements)

References 27 publications

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“…In a similar approach developed by Varinder Aggarwal, the electron-accepting properties of pyridinium salts, which can be easily prepared from amines, served as redox auxiliaries for EDA complex formation. Pyridinium derivatives 44 formed EDA-17 with Hantzsch ester 40 to generate alkyl radicals and promote a Giese addition to electron-poor olefins 45 (Figure b).…”

Section: Photoactivity Of Stoichiometric Eda Complexesmentioning

confidence: 99%

Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes

2020

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The association of an electron-rich substrate with an electron-accepting molecule can generate a new molecular aggregate in the ground state, called an electron donor−acceptor (EDA) complex. Even when the two precursors do not absorb visible light, the resulting EDA complex often does. In 1952, Mulliken proposed a quantum-mechanical theory to rationalize the formation of such colored EDA complexes. However, and besides a few pioneering studies in the 20th century, it is only in the past few years that the EDA complex photochemistry has been recognized as a powerful strategy for expanding the potential of visiblelight-driven radical synthetic chemistry. Here, we explain why this photochemical synthetic approach was overlooked for so long. We critically discuss the historical context, scientific reasons, serendipitous observations, and landmark discoveries that were essential for progress in the field. We also outline future directions and identify the key advances that are needed to fully exploit the potential of the EDA complex photochemistry.

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Section: Photoactivity Of Stoichiometric Eda Complexesmentioning

confidence: 99%

Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes

2020

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“…The Vilsmeier–Haack reagent has garnered interest from researchers since the day of its discovery and has been explored from different points of view. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 Acid chlorides, such as phosphorus pentachloride (PCl 5 ), 28 thionyl chloride, 29 phthaloyl dichloride, oxalyl chloride, 30 and phosphorus oxychloride (POCl 3 ), are used in reactions with dialkylformamides to generate the Vilsmeier–Haack reagent. The preparation of the Vilsmeier–Haack reagent is generally carried out by mixing POCl 3 and DMF at 0–5 °C, and it is one of the most commonly used reagents for the introduction of an aldehydic (CHO) group into electron-rich aromatic systems.…”

Section: Introductionmentioning

confidence: 99%

“…A wide variety of alkene derivatives, 14 carbonyl compounds, 15 and methylene 16 groups exhibit reactivity towards this reagent. In addition to carbon nucleophiles, several oxygen 17 and nitrogen 18 nucleophiles are also reactive towards the Vilsmeier–Haack reagent. We present herein the synthetic applications of the Vilsmeier–Haack reagent reported over the past 15 years.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Utility of the Vilsmeier–Haack Reagent in Organic Synthesis

Singh

Dohi

Kumar

et al. 2023

Synlett

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The Vilsmeier–Haack reaction has historically been a topic of significant interest to organic chemists, and it continues to attract considerable attention. The reaction itself provides a facile route towards a large number of aromatic and heteroaromatic systems. The Vilsmeier–Haack reagent, generated from amides and halides, is found to be very important in organic synthesis. This account highlights recent developments in the synthetic utility of the Vilsmeier–Haack reagent.1 Introduction2 Formylation3 Formylation and Chlorination4 Formylation and Acetylation5 Chlorination6 ortho-Formylation7 Miscellaneous8 Conclusions

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2,4,6-Triphenylpyrylium Tetrafluoroborate

Balaban

2001

Encyclopedia of Reagents for Organic Synthesis

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The non-chain radicaloid c-alkylation of nitronate anions: further evidence for the mechanism

Cited by 10 publications

References 27 publications

Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes

Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes

Synthetic Utility of the Vilsmeier–Haack Reagent in Organic Synthesis

2,4,6-Triphenylpyrylium Tetrafluoroborate

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