Copper‐Catalyzed Cleavage of Aryl C(OH)−C Bonds to Access Aryl Nitriles

Zheng, Yan; Liu, Wenbo; Ren, Yunlai; Guo, Yinggang; Tian, Xuan

doi:10.1002/slct.202103485

Cited by 6 publications

(2 citation statements)

References 74 publications

(18 reference statements)

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“…Traditionally, the production of nitriles primarily involves fossil resources, requires hazardous reagents, and generates a large amount of chemical waste, rendering more sustainable synthesis from renewable resources highly desirable . To date, a tremendous number of protocols have been developed to synthesize value-added bio-based nitriles from alcohol, , fatty acids, lignin, protein, and other renewable derivatives. For example, Sun’s team reported iron single-atom catalysts for the selective ammoxidation of alcohols to diverse aliphatic and aromatic mononitriles under mild conditions .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cyano-Containing Epoxy Precursor from Vanillin for Engineering Multifaceted Performance-Enhancing Resins

Zhao

Cao

et al. 2023

ACS Sustainable Chem. Eng.

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Interest in producing chemicals and thermosets from sustainable resources is growing, yet their moderate performance drastically undermines their potential applicability. Herein, an aryl dinitrile epoxy precursor (DVN-EP) was developed from vanillin. After curing with 4,4′-diaminodiphenyl sulfone (DDS), cyano-containing resin (DVN-EP/DDS) was produced with eminent comprehensive properties on account of the dual-cross-linked network formed by the epoxy-amine reaction and the further cyclotrimerization of cyano groups. In particular, the glass transition temperature, storage modulus, char yield (at 800 °C in N2), and Young’s modulus of the DVN-EP/DDS were 201 °C, 2795 MPa, 47.4%, and 5034 MPa, respectively, all much higher than those of the cyano-free counterpart (DMG-EP/DDS). Moreover, the cyano dipole–dipole pairings combined with the H-bonding interactions contributed to a tremendously increased lap shear strength of up to 7.18 MPa as well as good energy dissipation and damping capacity. The rationally designed dual-cross-linked network strengthening mechanism reported here offers an important and universal strategy for significantly enhancing the comprehensive properties of thermosets.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Cyano-Containing Epoxy Precursor from Vanillin for Engineering Multifaceted Performance-Enhancing Resins

Zhao

Cao

et al. 2023

ACS Sustainable Chem. Eng.

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“…Methods for the synthesis of aryl nitriles, including oxidative nitrogenation of aryl ethenes, , Ni-catalyzed cyanation of aryl thioethers and phenols, dehydrogenation of benzylamines, and condensation of aryl aldehydes with ammonia, have been established. Cu-catalyzed cleavage of aryl C(O)–C bonds and aryl C(OH)–C bonds have provided new entries to aryl nitriles. Recently, direct C–H cyanation has emerged as an efficient protocol to introduce cyano groups. − However, it is often limited to C(sp 2 )–H bonds or α-C(sp 3 )–H bonds of heteroatoms, and the regioselectivity remains a long-standing challenge.…”

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confidence: 99%

Fe-Catalyzed Direct Synthesis of Nitriles from Carboxylic Acids with Electron-Deficient N-Cyano-N-aryl–arylsulfonamide

Zhang

Tian

et al. 2023

Org. Lett.

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Established carboxylic acids to nitriles conversion methods suffer from expensive catalysts, tedious steps, high temperatures (>200 °C), high pressure, or a narrow substrate range. Herein, we demonstrate a concise and efficient access to diverse nitrile compounds from ubiquitous carboxylic acids with electron-deficient N-cyano-N-aryl–arylsulfonamide (NCAS) in moderate to excellent yields. This strategy is promoted by an inexpensive iron catalyst and is generally compatible with primary, secondary, tertiary, and aryl carboxylic acids, as well as a variety of functional groups.

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Catalyst‐Free Hydrogenolysis of Lignin β‐O‐4 Ketone Models with Water as an H‐transfer Reagent

Wang

et al. 2023

ChemistrySelect

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It was found that lignin β‐O‐4 ketone models could undergo smoothly the hydrogenolysis via light‐induced water‐donating transfer hydrogenation, which provides an example of using inexpensive and eco‐friendly water as the H‐transfer reagent to enable hydrogenolysis of lignin β‐O‐4 ketone models under catalyst‐free condition. Preliminary mechanistic investigations suggest that the mechanistic pathway involves the formation of acetophenone radicals.

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Copper‐Catalyzed Cleavage of Aryl C(OH)−C Bonds to Access Aryl Nitriles

Cited by 6 publications

References 74 publications

Synthesis of Cyano-Containing Epoxy Precursor from Vanillin for Engineering Multifaceted Performance-Enhancing Resins

Synthesis of Cyano-Containing Epoxy Precursor from Vanillin for Engineering Multifaceted Performance-Enhancing Resins

Fe-Catalyzed Direct Synthesis of Nitriles from Carboxylic Acids with Electron-Deficient N-Cyano-N-aryl–arylsulfonamide

Catalyst‐Free Hydrogenolysis of Lignin β‐O‐4 Ketone Models with Water as an H‐transfer Reagent

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