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

Zhang, Guodong; Zhang, Chengyu; Tian, Ye; Chen, Feng

doi:10.1021/acs.orglett.2c04185

Cited by 6 publications

(3 citation statements)

References 66 publications

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“…Methods for the synthesis of terminal E -configured alkenyl nitriles, including Fe-catalyzed deoxynitrogenation of carboxylic acids, , Ni or Rh-mediated hydrocyanation across carbon–carbon multiple bond, , and Fe-catalyzed direct functionalization of aryl ethenes, have been established. However, many of these methods require environmentally benign transition-metal catalysts.…”

Section: Resultsmentioning

confidence: 99%

Exploring Efficient Dual-Phase Emissive Fluorophores with High Mobility by Integrating a Rigid Donor and Flexible Acceptor

Guo,

Jin,

Zhang

et al. 2024

ACS Appl. Mater. Interfaces

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Developing luminogens with a high emission efficiency in both singlemolecule and aggregate states, as well as high mobility, shows promise for advancing the iteration and update of organic optoelectronic materials. However, achieving a delicate balance between the plane configuration of luminophores and the strong exciton interactions of aggregates is a formidable task from the molecular design perspective. This dilemma was overcome by integrating a rigid donor and flexible acceptor to establish donor−acceptor (D−A) type emitters. The π-conjugate-extended donor ensures the substantial planarity of these molecules, allowing strong emission in solution with photoluminescence quantum yield values of 86% and 75%. Furthermore, the restricted molecular motion of the aggregation-induced emission moiety and the formation of J-aggregates reduce the quenching effect, leading to a high emissive efficiency of 85% and 91% in the aggregate state. The mildly distorted D−A geometry builds moderate electrostatic interaction, resulting in high mobility with μ M,h of 7.12 × 10 −5 and 3.27 × 10 −4 cm 2 /V s. Additionally, an improved synthesized procedure for terminal E-configured acrylonitrile with metal-free and concise reaction conditions is presented. The successful application of the synthesized compounds in organic light-emitting diode devices demonstrates the practicability of the molecular design strategy with connecting a rigid donor and flexible acceptor.

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Section: Resultsmentioning

confidence: 99%

Exploring Efficient Dual-Phase Emissive Fluorophores with High Mobility by Integrating a Rigid Donor and Flexible Acceptor

Guo,

Jin,

Zhang

et al. 2024

ACS Appl. Mater. Interfaces

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“…Activated nitriles and �,�-unsaturated nitrile moieties are involved in a wide variety of natural plant products, drugs, colourants and agrochemicals (Fleming & Wang, 2003;Ahmed et al, 2022); they also represent versatile starting materials for the synthesis of a wide variety of therapeutically important heterocycles (Zhang et al, 2019;Metwally et al, 2023). The generally accepted importance of these functions (Wang et al, 2016;Hebishy et al, 2023) is reflected in the investment of much effort to synthesize them (Zhang et al, 2023;Elgemeie et al, 1998a,b). Recently, we have reported several new methods for the synthesis of pharmaceutically relevant heterocycles utilizing activated nitriles and �,�-unsaturated nitriles as starting materials (e.g.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 2,4-diamino-5-(4-hydroxy-3-methoxyphenyl)-8,8-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitrile–dimethylformamide–water (1/1/1)

Metwally,

Elgemeie,

Abd Al-latif

et al. 2024

Acta Cryst E

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In the structure of the title compound, C22H22N4O4·C3H7NO·H2O, the entire tricyclic system is approximately planar except for the carbon atom bearing the two methyl groups; the methoxyphenyl ring is approximately perpendicular to the tricycle. All seven potential hydrogen-bond donors take part in classical hydrogen bonds. The main molecule and the DMF combine to form broad ribbons parallel to the a axis and roughly parallel to the ab plane; the water molecules connect the residues in the third dimension.

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“…13 C{ 1 H} NMR (100 MHz, CDCl 3 , 298 K) δ (ppm) 133.6, 130.7, 129.0, 129.0, 127.0, 126. 4, 126.3, 125.7, 125.4, 122.3, 117.6, 21.6. Cinnamonitrile (3p): [60] Colourless oil. Yield 88 %.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

Dehydration of Amides by Redox‐Active Phenalenyl Based Mn‐Catalyst

2023

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A redox‐active phenalenyl ligand coordinated Mn(III)‐complex can be reduced chemically to generate an active catalyst containing a ligand‐centered radical. This chemically reduced Mn‐catalyst shows excellent catalytic reactivity for silylative dehydration of a wide range of primary amides (including late‐stage diversification of various bio‐active molecules) to synthesize nitriles using an inert and inexpensive silane, polymethylhydrosiloxane (PMHS), under mild conditions. Control experiments suggest a radical pathway for the present catalytic reaction, initiated by the ligand‐centered radical.

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

Cited by 6 publications

References 66 publications

Exploring Efficient Dual-Phase Emissive Fluorophores with High Mobility by Integrating a Rigid Donor and Flexible Acceptor

Exploring Efficient Dual-Phase Emissive Fluorophores with High Mobility by Integrating a Rigid Donor and Flexible Acceptor

Crystal structure of 2,4-diamino-5-(4-hydroxy-3-methoxyphenyl)-8,8-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitrile–dimethylformamide–water (1/1/1)

Dehydration of Amides by Redox‐Active Phenalenyl Based Mn‐Catalyst

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