Radical Reorganization Energies

Мирошниченко, Е. А.; Kon’kova, T. S.; Matyushin, Yu. N.; Orlov, Yu. D.; Pashchenko, L.L.; Vorob’ev, A. B.; Inozemtsev, A. V.

doi:10.1134/s1990793119020052

Cited by 6 publications

(7 citation statements)

References 11 publications

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“…General Remarks: 1 H, 13 C and 14 N NMR spectra were recorded with Bruker DRX-500 (500.1, 125.8, 36.1 MHz, respectively) and Bruker AV600 (600.1, 150.9, 43.4, respectively) spectrometers. Chemical shifts are reported in delta (δ) units, parts per million (ppm) downfield from internal TMS ( 1 H, 13 C) or external CH 3 NO 2 ( 14 N, negative values of δ N correspond to upfield shifts).…”

Section: Methodsmentioning

confidence: 99%

“…The resulting solution was concentrated under reduced pressure at 0°C to a volume of ≈ 0.5 mL and 1,1,2,2-tetrachloroethane (38 mg, 0.23 mmol) was added to the residue as quantitative internal standard. The 1 H, 13 C and 14 N NMR spectra were recorded. According to 1 H NMR the sample contained nitro(nitro-NNO-azoxy)methane (1) (68 mg, 45 %).…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (600.13 MHz, CDCl 3 ): δ = 6.32 (s, 2 H, CH 2 ) ppm. 13 C NMR (150.9 MHz, CDCl 3 ): δ = 93.1 (br., CH 2 ) ppm. 13 C NMR (without proton decoupling, 150.9 MHz, CDCl 3 ): δ = 93.1 (br.…”

Section: Methodsmentioning

confidence: 99%

“…DSC (5°C min -1 ): 88°C (dec.). 1 H NMR (500.1 MHz, CDCl 3 ): δ = 1.38 (s, 9 H, CMe 3 ), 6.05 (s, 2 H, CH 2 ) ppm 13. C NMR (125.8 MHz, CDCl 3 ): δ = 25.1 (CMe 3 ), 60.8 (CMe 3 ), 90.9 (br., CH 2 ) ppm 13.…”

mentioning

confidence: 99%

“…1 H NMR (500.1 MHz, CDCl 3 ): δ = 1.38 (s, 9 H, CMe 3 ), 6.05 (s, 2 H, CH 2 ) ppm 13. C NMR (125.8 MHz, CDCl 3 ): δ = 25.1 (CMe 3 ), 60.8 (CMe 3 ), 90.9 (br., CH 2 ) ppm 13. C NMR (without proton decoupling, 125.8 MHz, CDCl 3 ): δ = 25.1 (q, 1 J H,C = 128.7 Hz, CMe 3 ), 60.8 (dec., 2 J H,C = 4.0 Hz, CMe 3 ), 90.9 (br.…”

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confidence: 99%

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First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds

et al. 2018

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The first aliphatic nitro‐NNO‐azoxy compounds were synthesized by substitutive nitration of appropriate tert‐butyl‐NNO‐azoxy compounds with nitronium tetrafluoroborate. Nitro(nitro‐NNO‐azoxy)methane (1), (tert‐butyl‐NNO‐azoxy)(nitro‐NNO‐azoxy)methane (2), bis(nitro‐NNO‐azoxy)methane (3), and 2‐nitro‐2‐(nitro‐NNO‐azoxy)propane (4) were prepared. Compound 4 with the nitro‐NNO‐azoxy group bound with the tertiary C atom appeared most stable (DSC, onset temperature of decomposition 104 °C). Compound 2 was less stable (DSC, onset temperature 88 °C). Compounds with strong electron withdrawing substituents had the least stability, assumingly, due to rather high acidity of CH protons alongside with instability of C‐anions of nitro‐NNO‐azoxy compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds

et al. 2018

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Photoredox‐ and Nickel‐Catalyzed Hydroalkylation of Alkynes with 4‐Alkyl‐1,4‐dihydropyridines: Ligand‐Controlled Regioselectivity

Zhang

Tanabe

Kuriyama

et al. 2022

Chemistry A European J

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Dual photoredox‐ and nickel‐catalyzed hydroalkylation of terminal alkynes with 4‐alkyl‐1,4‐dihydropyridines under visible light irradiation to afford Markovnikov‐ or anti‐Markovnikov‐type alkylated alkenes in good‐to‐high yields has been achieved, in which the regioselectivity of the products was effectively controlled by coordination ligands for nickel species. Using [NiCl2(dtbbpy)] as a catalyst led to the formation of Markovnikov‐type products, whereas using NiCl2 ⋅ 6 H2O led to the formation of anti‐Markovnikov‐type products.

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Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals

et al. 2023

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Transition metal-catalyzed enantioselective free radical substitution reactions have recently attracted attention as convenient and important building tools in synthetic chemistry, although construction of stereogenic carbon centers at the propargylic position of propargylic alcohols by reactions with free radicals remains unchallenged. Here we present a strategy to control enantioselective propargylic substitution reactions with alkyl radicals under photoredox conditions by applying dual photoredox and diruthenium catalytic system, where the photoredox catalyst generates alkyl radicals from 4-alkyl-1,4-dihydropyridines, and the diruthenium core with a chiral ligand traps propargylic alcohols and alkyl radicals to guide enantioselective alkylation at the propargylic position, leading to high yields of propargylic alkylated products containing a quaternary stereogenic carbon center at the propargylic position with a high enantioselectivity. The result described in this paper provides the successful example of transition metal-catalyzed enantioselective propargylic substitution reactions with free alkyl radicals.

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Radical Reorganization Energies

Cited by 6 publications

References 11 publications

First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds

First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds

Photoredox‐ and Nickel‐Catalyzed Hydroalkylation of Alkynes with 4‐Alkyl‐1,4‐dihydropyridines: Ligand‐Controlled Regioselectivity

Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals

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