Oxidation of secondary aliphatic amines in systems containing sodium peroxydisulfate

Troyanskii, E. I.; Ioffe, V. A.; Nikishin, G. I.

doi:10.1007/bf00948513

Cited by 5 publications

(3 citation statements)

References 11 publications

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“…1 H NMR (500 MHz, CDCl 3 ): δ 3.60 (t, J = 7.8 Hz, 1H), 2.62–2.55 (m, 2H), 2.37 (ddd, J = 13.1, 8.4, 4.8 Hz, 2H), 1.80–1.67 (m, 2H), 1.52–1.25 (m, 16H), 0.98–0.89 (m, 9H) ppm. The spectral data were in agreement with literature data …”

Section: Methodssupporting

confidence: 90%

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Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

2018

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This paper describes the development and mechanistic studies of a general, high-yielding amine C-H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient C-H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology. Mechanistic studies suggest that the carboxylic acid additive has three effects: formation of a stabilizing hemiaminal intermediate, prevention of catalyst decomposition by protonating the substrate, and modulation of fluorescence quenching of the photoexcited catalyst species.

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Section: Methodssupporting

confidence: 90%

“…The spectral data were in agreement with literature data. 52 2-(Dibenzylamino)-2-phenylacetonitrile (14a). Eluent: 1:9 EtOAc/hexane.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

2018

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“…2‐(Dibutylamino)pentanenitrile (34): Following General Procedure A , tributylamine 33 (0.24 mL, 1.0 mmol) was reacted with Me 3 SiCN (270 μL, 2.00 mmol) for 27 h. The crude product was purified by column chromatography (SiO 2 , pentane/Et 2 O=40:1) to give 34 as a colorless viscous liquid; yield: 145 mg (69%); known compound; the 1 H NMR spectroscopic data agree with those given in ref 56 . 1 H NMR (CDCl 3 , 300 MHz): δ =0.89–0.97 (m, 9 H), 1.21–1.54 (m, 10 H), 1.66–1.75 (m, 2 H), 2.30–2.38 (m, 2 H), 2.52–2.62 (m, 2 H), 3.58 (t, J =7.7 Hz, 1 H); 13 C NMR (CDCl 3 , 75.5 MHz): δ =13.6, 14.1, 19.4, 20.5, 30.4, 34.1, 51.6, 54.5, 118.7; IR (neat/ATR probe): ν =2958, 2932, 2873, 2823, 1467, 1379, 1309, 1261, 1170, 1116, 1091, 877, 801, 741 cm −1 ; HR‐MS (EI): m/z =210.2106, calcd.…”

Section: Methodssupporting

confidence: 58%

Multifunctional Nitrogen‐Doped Carbon Nanodots for Photoluminescence, Sensor, and Visible‐Light‐Induced H₂ Production

et al. 2015

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Herein, multifunctional N-doped carbon nanodots (NCNDs) were prepared through the one-step hydrothermal treatment of yeast. Results show that the NCNDs can be used as a new photocatalyst to drive the water-splitting reaction under UV light. Moreover, the NCNDs can efficiently catalyze the hydrogen evolution reaction. Under visible-light irradiation, Eosin Y-sensitized NCNDs exhibit excellent activity for hydrogen evolution. The hydrogen evolution rate of NCNDs (without any modification and co-catalyst) reaches 107.1 μmol h(-1) (2142 μmol g(-1) h(-1) ). When Pt is loaded on the NCNDs, the hydrogen evolution rate reaches 491.2 μmol h(-1) (9824 μmol g(-1) h(-1)) under visible-light irradiation. In addition, the NCNDs show excellent fluorescent properties and can be applied as a fluorescent probe for the sensitive and selective detection of Fe(3+) .

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Ammonium Peroxydisulfate

Behrman

2001

Encyclopedia of Reagents for Organic Synthesis

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Oxidation of secondary aliphatic amines in systems containing sodium peroxydisulfate

Cited by 5 publications

References 11 publications

Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

Multifunctional Nitrogen‐Doped Carbon Nanodots for Photoluminescence, Sensor, and Visible‐Light‐Induced H₂ Production

Ammonium Peroxydisulfate

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Oxidation of secondary aliphatic amines in systems containing sodium peroxydisulfate

Cited by 5 publications

References 11 publications

Photoredox-Catalyzed Cα–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

Photoredox-Catalyzed Cα–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

Multifunctional Nitrogen‐Doped Carbon Nanodots for Photoluminescence, Sensor, and Visible‐Light‐Induced H2 Production

Ammonium Peroxydisulfate

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Product

Resources

About

Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

Multifunctional Nitrogen‐Doped Carbon Nanodots for Photoluminescence, Sensor, and Visible‐Light‐Induced H₂ Production