Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

Ruan, Shixiang; Ruan, Jiancheng; Chen, Xinzhi; Zhou, Shaodong

doi:10.1016/j.mcat.2020.111313

Cited by 6 publications

(14 citation statements)

References 63 publications

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“…51% yield; yellow oil liquid; E/Z = 78/22; purification by silica gel chromatography (petroleum ether/ethyl acetate = 30 : 1) 1 H NMR (400 MHz, Chloroform-d) δ 7.26 (t, J = 8.0 Hz, 2H), 6.75-6.71 (m, 3H), 6.42 (t, J = 7.7 Hz, 22/100 × 1H), 6.17 (t, J = 7.7 Hz, 78/100 × 1H), 3.58-3.53 (m, 2H), 2.98 (s, 22/100 × 3H), 2.97 (s, 78/100 × 3H), 2.47 (t, J = 7.2 Hz, 2H), 2.36 (q, J = 7.3 Hz, 78/100 × 2H), 2.14-2.06 (m, 22/100 × 2H), 1.43-1.27 (m, 4H), 0.92 (t, J = 7.0 Hz, 78/100 × 3H), 0.87 (t, J = 7.0 Hz, 22/100 × 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 150.…”

Section: -(2-(methyl(phenyl)amino)ethyl)hept-2-enenitrile(3 Da)mentioning

confidence: 99%

“…reaction time (4 h); 59% yield; yellow oil liquid; E/Z = 70/30; purification by silica gel chromatography (petroleum ether/ ethyl acetate = 30 : 1) 1 H NMR (500 MHz, Chloroform-d) δ 7.61 (d, J = 7.9 Hz, 70/100 × 2H), 7.30-7.22 (m, 70/100 × 4H + 30/100 × 2H), 7.15 (s, 30/100 × 4H), 6.89 (s, 70/100 × 1H), 6.80-6.70 (m, 3H + 30/100 × 1H), 3.67 (t, J = 6.9 Hz, 2H), 3.00 (s, 70/100 × 3H), 2.96 (s, 30/100 × 3H), 2.75 (d, J = 7.4 Hz, 30/100 × 2H), 2.66 (t, J = 7.1 Hz, 70/100 × 2H), 2.39 (s, 70/100 × 3H), 2.37 (s, 30/100 × 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 148.…”

Section: -(Methyl(phenyl)amino)-2-(4-methylbenzylidene)butanenitrile(...mentioning

confidence: 99%

“…reaction time (4 h); 60% yield; yellow oil liquid; E/Z = 66/34; purification by silica gel chromatography (petroleum ether/ ethyl acetate = 10 : 1) 1 H NMR (500 MHz, Chloroform-d) δ 7.72-7.69 (m, 66/100 × 2H), 7.31-7.21 (m, 66/100 × 4H + 34/100 × 2H), 6.95-6.93 (m, 34/100 × 4H), 6.86 (d, J = 8.6 Hz, 66/100 × 2H), 6.78-6.72 (m, 2H + 34/100 × 2H), 3.85 (s, 66/100 × 3H), 3.83 (s, 34/100 × 3H), 3.67 (q, J = 7.2, 6.5 Hz, 2H), 3.01 (s, 66/100 × 3H), 2.98 (s, 34/100 × 3H), 2.77-2.74 (m, 34/100 × 2H), 2.64 (d, J = 7.0 Hz, 66/100 × 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 161.…”

Section: -(4-methoxybenzylidene)-4-(methyl(phenyl)amino)butanenitrile...mentioning

confidence: 99%

“…reaction time (4 h); 63% yield; yellow oil liquid; E/Z = 65/35; purification by silica gel chromatography (petroleum ether/ ethyl acetate = 30 : 1) 1 H NMR (500 MHz, Chloroform-d) δ 7.68 (d, J = 8.2 Hz, 65/100 × 2H), 7.33-7.20 (m, 5H + 35/100 × 1H), 6.92 (s, 65/100 × 1H), 6.80-6.72 (m, 3H), 3.71-3.67 (m, 2H), 3.02 (s, 65/100 × 3H), 2.99 (s, 35/100 × 3H), 2.98-2.91 (m, 1H), 2.79-2.76 (m, 35/100 × 2H), 2.70-2.67 (m, 65/100 × 2H), 1.29 (dd, J = 6.9, 5.4 Hz, 6H). 13 C NMR (126 MHz, CDCl 3 ) δ 151.…”

Section: -(4-isopropylbenzylidene)-4-(methyl(phenyl)amino)butanenitri...mentioning

confidence: 99%

“…)butanenitrile(3 bc): reaction time (6 h); 64% yield; yellow oil liquid; E/Z = 69/31; purification by silica gel chromatography (petroleum ether/ ethyl acetate = 30 : 1) 1 H NMR (500 MHz, Chloroform-d) δ 7.08 (dd, J = 8.6, 3.4 Hz, 2H), 6.68-6.64 (m, 2H), 6.24 (d, J = 10.1 Hz, 31/ × 100H), 5.98 (d, J = 9.9 Hz, 69/100 × 1H), 3.55-3.51 (m, 2H), 2.97 (s, 93/100 × 3H), 2.94 (s, 69/100 × 3H), 2.58-2.51 (m, 69/100 × 1H), 2.49 (d, J = 7.2 Hz, 1H), 2.44 (t, J = 7.1 Hz, 1H), 2.29 (d, J = 2.0 Hz, 3H), 1.76-1.09 (m, 10H). 13 C NMR (126 MHz, CDCl 3 ) δ 154.…”

Section: -(Cyclohexylmethylene)-4-(methyl(p-tolyl)aminomentioning

confidence: 99%

See 4 more Smart Citations

Synthesis of Acrylonitrile Derivatives via Visible Light‐induced Coupling Reaction of Morita‐Baylis‐Hillman Adducts with Tertiary Amines and α‐Trimethylsilyl Amines

Chen

Ding

et al. 2021

Asian J Org Chem

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Ru-catalyzed coupling reaction of Morita-Baylis-Hillman (MBH) adducts with tertiary amines and α-trimethylsilyl amines under visible light is disclosed. Compared with the reported MBH adducts with ester as withdrawing-electron groups, MBH adducts with cyano group in this paper show different chemical reaction characteristics. The universality of substrates has been extended. A series of structurally complementary acrylonitriles are obtained in satisfied yields under mild condition, which provides a good opportunity to discover new meaningful bioactive compounds.

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Section: -(2-(methyl(phenyl)amino)ethyl)hept-2-enenitrile(3 Da)mentioning

confidence: 99%

Section: -(Methyl(phenyl)amino)-2-(4-methylbenzylidene)butanenitrile(...mentioning

confidence: 99%

Section: -(4-methoxybenzylidene)-4-(methyl(phenyl)amino)butanenitrile...mentioning

confidence: 99%

Section: -(4-isopropylbenzylidene)-4-(methyl(phenyl)amino)butanenitri...mentioning

confidence: 99%

Section: -(Cyclohexylmethylene)-4-(methyl(p-tolyl)aminomentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Acrylonitrile Derivatives via Visible Light‐induced Coupling Reaction of Morita‐Baylis‐Hillman Adducts with Tertiary Amines and α‐Trimethylsilyl Amines

Chen

Ding

et al. 2021

Asian J Org Chem

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Dehydration of Amides to Nitriles over Heterogeneous Silica‐Supported Molybdenum Oxide Catalyst

et al. 2022

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Silica‐supported molybdenum oxide (MoOx/SiO2) with 4.8 wt% Mo (0.5 mmol g−1) was an effective and reusable heterogeneous catalyst for dehydration of 2‐furamide to 2‐furonitrile (96 % yield). The catalyst was applicable to the dehydration of various amides including heteroaromatic, aromatic and alkyl amides, providing the corresponding nitriles in high yields (87‐97 %). Based on the results of catalyst characterizations (XRD, TEM, UV‐vis, Raman) and activity tests, MoOx species are highly dispersed over SiO2, and heptamolybdate anion ([Mo7O24]6−) and isolated dioxo ((O=)2MoO2) were mainly formed on the SiO2 support of the optimal MoOx/SiO2 catalyst. The strong Brønsted acid sites (Mo‐OH−Si site) can be formed from the MoOx species and the adjacent silanol group, and the acid‐base pair site (Mo(=O)−OH−Si site) of the strong Brønsted acid site (Mo−OH−Si site) and base site (Mo=O) over MoOx/SiO2 catalyst could be the main active site for the dehydration of amides.

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Engineered aldoxime dehydratase to enable the chemoenzymatic conversion of benzyl amines to aromatic nitriles

Xiao

Feng

Chen

et al. 2023

Bioorganic Chemistry

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Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

Cited by 6 publications

References 63 publications

Synthesis of Acrylonitrile Derivatives via Visible Light‐induced Coupling Reaction of Morita‐Baylis‐Hillman Adducts with Tertiary Amines and α‐Trimethylsilyl Amines

Synthesis of Acrylonitrile Derivatives via Visible Light‐induced Coupling Reaction of Morita‐Baylis‐Hillman Adducts with Tertiary Amines and α‐Trimethylsilyl Amines

Dehydration of Amides to Nitriles over Heterogeneous Silica‐Supported Molybdenum Oxide Catalyst

Engineered aldoxime dehydratase to enable the chemoenzymatic conversion of benzyl amines to aromatic nitriles

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