Copper-catalyzed formation of N,N-dimethyl benzamide from nitrile and DMF under an O2 atmosphere

Hu, Chenxu; Yan, Xufei; Zhou, Xiangge; Li, Zhengkai

doi:10.1039/c3ob41855c

Cited by 25 publications

(8 citation statements)

References 51 publications

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“…N , N -Dimethylformamide (DMF) is a popular, inexpensive, aprotic polar solvent, which is widely used as a solvent in various organic reactions . DMF is also used as a reagent and a multipurpose precursor for the introduction of various functional groups such as −CHO, −CO, −CON(CH 3 ) 2 , −N(CH 3 ) 2 , −CN, =CH, and −H moieties in organic chemistry. Li and co-workers recently reported a transition-metal-free approach for the synthesis of 2-aryliminochromenes from arynes, N,S-keteneacetals, and DMF, where DMF was used as a source of oxygen to form the chromeneskeleton .…”

mentioning

confidence: 99%

N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

Liu

Zhou

2017

J. Org. Chem.

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An unprecedented α-hydroxylation strategy was developed for the synthesis of α-hydroxy arones using N,N-dimethylformamide (DMF) as an oxygen source. Control experiments demonstrated that the oxygen atom of the hydroxy group in the α-hydroxy arones produced in this reaction was derived from DMF. This new reaction therefore not only provides an alternative strategy for the α-hydroxylation of arones but also highlights the possibility of using the inexpensive common solvent DMF as a source of oxygen in organic synthesis.

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mentioning

confidence: 99%

N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

Liu

Zhou

2017

J. Org. Chem.

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“…Benzyl nitriles have been recently identified as promising substrates for copper‐promoted amidation as evidenced by recent reports. Li and co‐workers utilized substituted arylacetonitriles 165 along with N,N ‐dimethylformamide as solvent with a copper phenanthrene catalyst under an oxygen atmosphere to provide N,N ‐dimethyl benzamides 166 in good yields (Scheme ) . However, p ‐toluenesulfonic acid as an equimolar additive as well as the required elevated reaction temperature limit the applicability of this method to a certain extent.…”

Section: Amidesmentioning

confidence: 99%

Recent Trends in Copper‐Catalyzed C−H Amination Routes to Biologically Important Nitrogen Scaffolds

Subramanian

Rudolf

Kaliappan

2015

Chemistry An Asian Journal

109

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Nitrogen-containing heterocycles have found remarkable applications in natural product research, material sciences, and pharmaceuticals. Although the synthesis of this interesting class of compounds attracted the interest of generations of organic chemists, simple and straightforward assembly methods based on transition-metal catalysis have regularly been elusive. The recent advancements in the development of C-H functionalization have helped in accomplishing the synthesis of a variety of complex heterocycles from simple precursors. This Focus Review summarizes the recent advances in one particular field: the copper-catalyzed C-N bond formation reactions via C-H bond functionalization to furnish a comprehensive range of nitrogen heterocycles. Applicability and synthetic feasibility of a particular reaction represent major requirements for the inclusion in this review.

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“…In recent years, the use of various transition metal catalysts for oxidative amidation reaction of alcohols/TBHP has been reported to be able to directly synthesize benzamides has become a hot topic. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Transition metal-containing phthalocyanine compounds show interesting capabilities in the catalytic oxidation of many organic reactions. [21][22][23] Phthalocyanine is an artificially synthesized planner big ring compound.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF₃) Substituted Copper Phthalocyanine Based Composite Catalyst

et al. 2021

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Using a type of tetra‐substituted metal phthalocyanine carbon nanotubes composite material [4 a (OPh‐p‐CF3)CuPc]‐MWCNTs as a catalyst, a method to synthesize benzamides through the oxidative amidation of benzyl alcohol was developed. Synthesize copper phthalocyanine by simple DBU liquid phase catalytic method, and then load phthalocyanine on carbon nanotubes by ultrasound to form four‐substituted metal phthalocyanine carbon nanotubes composite material [4 a (OPh‐p‐CF3)CuPc]‐MWCNTs. The composite materials were detected by ultraviolet visible spectroscopy (UV‐Vis), Fourier transforms infrared spectroscopy (FT‐IR), X‐ray diffraction spectroscopy (XRD), scanning electron microscope (SEM) and transmission electron microscope (TEM). To achieve high‐efficiency and optional catalyze, studied solvent type, oxidant type and dosage, catalyst dosage, time and temperature. In the screening experiment, [4 a (OPh‐p‐CF3)CuPc]‐MWCNTs composite material has high catalytic ability in the oxidation of benzyl alcohol. At the greatest of times, the highest conversion ratio of benzyl alcohol (100 %), selectivity of benzamide (89 %) was obtained. The oxidant was TBHP and the amount was 3 mL, 60 °C for 24 h in DMF. Different kinds of amides were set up by various substituted benzyl alcohols, and good results were obtained.

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Copper-catalyzed formation of N,N-dimethyl benzamide from nitrile and DMF under an O2 atmosphere

Abstract: Amidation of nitrile with N,N-dimethylformamide (DMF) was catalyzed by Cu2O with 1,10-phenanthroline as a ligand under an oxygen atmosphere. A variety of N,N-dimethyl benzamides were obtained in yields up to 84%.

Cited by 25 publications

References 51 publications

N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

Recent Trends in Copper‐Catalyzed C−H Amination Routes to Biologically Important Nitrogen Scaffolds

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF₃) Substituted Copper Phthalocyanine Based Composite Catalyst

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Copper-catalyzed formation of N,N-dimethyl benzamide from nitrile and DMF under an O2 atmosphere

Abstract: Amidation of nitrile with N,N-dimethylformamide (DMF) was catalyzed by Cu2O with 1,10-phenanthroline as a ligand under an oxygen atmosphere. A variety of N,N-dimethyl benzamides were obtained in yields up to 84%.

Cited by 25 publications

References 51 publications

N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

Recent Trends in Copper‐Catalyzed C−H Amination Routes to Biologically Important Nitrogen Scaffolds

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF3) Substituted Copper Phthalocyanine Based Composite Catalyst

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Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF₃) Substituted Copper Phthalocyanine Based Composite Catalyst