Sonochemical protocols for Grignard reactions

Smolnikov, Sergei A.; Shahari, Muhammad Syafiq Bin; Dolzhenko, Anton V.

doi:10.1016/b978-0-12-819540-6.00009-7

Cited by 3 publications

(5 citation statements)

References 23 publications

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“…The combined organic phases were dried (Na2SO4), and the volatiles were removed under reduced pressure to yield the 1b as a brown viscous liquid (6. 5…”

Section: Synthesis Of the Dialdehyde S(c6h4cho)2 (1b)mentioning

confidence: 99%

“…In this vein, halogen-by-halogen exchange substitution provides a convenient route for synthesizing alkyl halides [4]. Other typical and very useful reaction of alkyl halides involves the formation of free radicals in the presence of very active alkaline or alkaline earth metals; subsequent reaction of these radicals can lead to the formation of organometallic compounds or coupling of the alkyl radicals to enlarge carbon chains [5].…”

Section: Introductionmentioning

confidence: 99%

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Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

García-González,

Alvarado-Rodríguez,

Andrade-López

et al. 2024

J. Mex. Chem. Soc.

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Abstract. In this work, the synthesis and structural study by means of single-crystal X-ray diffraction of compounds of general formula Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I) is reported. These compounds contain two flexible hydrocarbonated arms –CH2–X in the ortho positions to the Ch heteroatom. These compounds were synthesized through a linear synthesis starting from diphenylether or diphenylsulfide. Based on the structural analysis, we describe the more relevant molecular features as well as the non-covalent interactions that the heavy halogen atoms display with other moieties that promote the cohesion of the crystal arrangement. The Hirshfeld analysis displayed that the X···π, X···X, and C–H···X interactions are quite significant in the crystal arrangement. Resumen. En este trabajo, se describen la síntesis y el estudio estructural de difracción de rayos-X de monocristal de seis compuestos con fórmula general Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I), que contienen dos brazos hidrocarbonados flexibles –CH2–X en las posiciones orto al heteroátomo Ch. Estos compuestos fueron sintetizados a través de una síntesis lineal, partiendo de difeniléter o difeniltioéter. A través del análisis estructural se describen las características moleculares más relevantes, así como las interacciones no-covalentes que presentan los átomos de halógeno pesados con otros grupos funcionales para dar cohesión a la red cristalina. El estudio de las superficies de Hirshfeld mostró que las interacciones X···π, X···X y C–H···X son muy relevantes en esta cohesión.

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“…The combined organic phases were dried (Na2SO4), and the volatiles were removed under reduced pressure to yield the 1b as a brown viscous liquid (6. 5…”

Section: Synthesis Of the Dialdehyde S(c6h4cho)2 (1b)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

García-González,

Alvarado-Rodríguez,

Andrade-López

et al. 2024

J. Mex. Chem. Soc.

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“…Además, la turbulencia contribuye haciendo chocar las partículas, resultando en cambios morfológicos. También se ha demostrado que en algunos casos puede mejorar la selectividad de las reacciones, haciendo práctica la reacción de Barbier (en un solo paso) (Smolnikov, Shahari, & Dolzhenko, 2020).…”

Section: Activación De Mgunclassified

Reacciones de Grignard: más de cien años de relevancia

Duarte-León,

Alvarado-Rodríguez,

García-González

et al. 2023

ICBI

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Los reactivos de Grignard han sido los compuestos organometálicos más utilizados de los últimos cien años. Al final del siglo XIX, en la Universidad de Lyon, Antoine Barbier modificó el método Wagner-Saytzeff mediante el intercambio de Zn por Mg en la síntesis de alcoholes en un solo paso, a partir de halogenuros orgánicos y compuestos carbonílicos. Posteriormente, su estudiante doctoral Victor Grignard estudió esa modificación de una forma más detallada. Él identificó la especie reactiva como RMgX, y concluyó que podría mejorar los rendimientos de sus reacciones al preparar primero a esta especie para posteriormente adicionarla al compuesto carbonílico. La síntesis de los reactivos de Grignard está fuertemente influenciada por factores diversos como los disolventes usados, la forma de activar al magnesio o la naturaleza del halogenuro orgánico empleado. Estos compuestos organomagnésicos tienen gran importancia en la química sintética debido a que se comportan como nucleófilos capaces de formar enlaces carbono-carbono o carbono-heteroátomo.

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“…6 In recent years, researchers have explored various approaches for improving the Grignard reaction, including the utilization of ionic liquids, 7 microwaves, 8,9 and ultrasounds. 10,11 However, there is currently no existing literature on the application of electrooxidation as a method for conducting the Grignard reaction. Traditional Grignard reactions indeed have limitations such as sensitivity to air and moisture, a restricted range of compatible substrates, and the use of various activating agents, such as iodine, to activate magnesium and ethyl bromide as a Grignard reagent.…”

Section: Introductionmentioning

confidence: 99%

“…The Grignard reaction is a well‐established technique for introducing functional groups and forging carbon–carbon bonds in organic compounds 6 . In recent years, researchers have explored various approaches for improving the Grignard reaction, including the utilization of ionic liquids, 7 microwaves, 8,9 and ultrasounds 10,11 . However, there is currently no existing literature on the application of electrooxidation as a method for conducting the Grignard reaction.…”

Section: Introductionmentioning

confidence: 99%

Producing p‐tolylmethanol derivatives through an eco‐friendly electro‐organic method: A highly efficient Grignard reaction utilizing a magnesium electrode

Abdullaev,

Alaridhee,

Abdullah

et al. 2024

Applied Organom Chemis

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This research introduces an eco‐friendly and innovative technique for efficiently producing p‐tolylmethanol derivatives 4(a–k) using electro‐organic synthesis based on the Grignard reaction. By employing electrochemical methods, this approach offers several advantages, including enhanced reaction efficiency and reduced environmental impact. The process involves the electrochemical generation of the Grignard reagent, followed by its reaction with appropriate substrates to yield the desired p‐tolylmethanol derivatives. Our team optimized various reaction parameters like choice of solvent, electrode material, and reaction conditions to achieve high yields and selectivity. The developed electro‐organic method demonstrated outstanding efficiency and presents a fresh and environmentally conscious approach to synthesizing p‐tolylmethanol derivatives from benzaldehyde 1(a–e) and bromobenzene 2(a–h) via the Grignard reaction, yielding excellent results (85–93%). The resulting compounds were comprehensively characterized using melting point, 1H NMR spectroscopy, and CHN analysis to verify their structures. This electro‐organic approach holds significant potential as a sustainable strategy for synthesizing valuable organic compounds.

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Sonochemical protocols for Grignard reactions

Cited by 3 publications

References 23 publications

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

Reacciones de Grignard: más de cien años de relevancia

Producing p‐tolylmethanol derivatives through an eco‐friendly electro‐organic method: A highly efficient Grignard reaction utilizing a magnesium electrode

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