Visible light-mediated intramolecular C–H arylation of diazonium salts of N-(2-aminoaryl)benzoimines: a facile synthesis of 6-arylphenanthridines

Natarajan, Palani; Kumar, Naresh; Sharma, Manjeet

doi:10.1039/c6qo00275g

Cited by 32 publications

(8 citation statements)

References 46 publications

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“…2C). 24 With this FDPP:PdPc system, it is possible to use NIR light to promote reactions which require photocatalysts that absorb green or yellow light, but most organometallic photocatalysts absorb higher energy blue or UV light iv . We found that it is possible to use NIR absorbing sensitizer, Platinum (II) tetraphenyltetranaphthoporphyrin (PtTPTNP) 25,26 together with a simple blue emitting annihilator, TTBP, to generate NIR-to-blue photon upconversion, with an upconversion yield as high as 2.0% (Fig.…”

mentioning

confidence: 99%

Photoredox catalysis using infrared light via triplet fusion upconversion

Ravetz

Pun

Churchill

et al. 2019

Nature

546

565

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mentioning

confidence: 99%

Photoredox catalysis using infrared light via triplet fusion upconversion

Ravetz

Pun

Churchill

et al. 2019

Nature

546

565

View full text Add to dashboard Cite

“…disclosed a visible‐light mediated synthesis of 6‐arylphenanthridines using aryl diazonium salts formed in situ from the reactions of N‐( 2‐aminoaryl)benzoimines and TBN. This visible light‐mediated protocol shows certain merits over reported methods for the synthesis of 6‐arylphenanthridines viz ., use of economical reagents and the mild reaction conditions …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

“…This visible light-mediated protocol shows certain merits over reported methods for the synthesis of 6-arylphenanthridines viz.,u se of economical reagents and the mild reactionconditions. [39] In the past decades, continuous-flow synthesis has come to the fore as an important technology because hazardousr eactions can be safely carriedo ut.K eepingt his in mind, Jamison group developed am ethod for the synthesis of highly substituted pyrazoles (26)a nd pyrazolines (26')f rom 2,2-difluoromethyl diazomethane (25)a nd 2,2,2-trifluoromethyl diazomethane (25')( generated in situ by reacting fluorinated amines and TBN) in au nified continuous flow assembly-line. The synthetic utility of the presentp rotocolw as shown by the synthesis of measles therapeutic AS-136A in 75 %y ield with 99 % purity (Scheme 19).…”

Section: Diazotizationmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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“…Moreover, the ruthenium(II) complex has emerged as efficient photosensitizers for catalyzing C–H arylations of aryl diazonium salts. − In 2014, the direct arylation of N -heteroarenes with aryl diazonium salts was successfully implemented in water, using Ru(bpy) 3 Cl 2 ·6H 2 O as a photosensitizer and a commercial household light bulb as a light source (Scheme ). This water-phase arylation reaction provides a variety of arylated heterocycle scaffolds including xanthene, thiazole, pyrazine, pyridazine, and pyridine with good regioselectivity.…”

Section: Aryl C–c Bond Formationsmentioning

confidence: 99%

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

et al. 2021

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Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance of aryl diazonium salts spanning most disciplines of the chemical sciences, we review the recent development of aryl diazonium chemistry over the past seven years (2013−2020). Special emphasis is put on various new transformations involving the generation of radical intermediates via thermal, photochemical, and electrochemical means. Recent advances in the development of transition metal-catalyzed reactions using aryl diazonium salts are also reviewed. Together, these newly developed transformations significantly expand the synthetic chemist's repertoire of aromatic carbon−carbon and carbon−heteroatom bond forming methods using aryl diazonium precursors, providing powerful tools for the synthesis and modification of complex molecular scaffolds.

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Visible light-mediated intramolecular C–H arylation of diazonium salts of N-(2-aminoaryl)benzoimines: a facile synthesis of 6-arylphenanthridines

Abstract: 6-Arylphenanthridines were synthesized in good to excellent yields from inexpensive and environmentally benign N-(2-aminoaryl)-diphenylmethanimine as a starting material under visible light-photocatalyzed conditions.

Cited by 32 publications

References 46 publications

Photoredox catalysis using infrared light via triplet fusion upconversion

Photoredox catalysis using infrared light via triplet fusion upconversion

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

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