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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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E1 Reaction: Kinetics and Mechanism02:46

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Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
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Acoplamiento C-C y C-H mediado por sustrato después de la deshalogenación

Huihui Kong, Sha Yang, Hongying Gao1,2

  • 1Physikalisches Institut, Westfälische Wilhelms-Universität Münster , Wilhelm-Klemm-Strasse 10, 48149 Münster, Germany.

Journal of the American Chemical Society
|February 11, 2017
PubMed
Resumen

Los investigadores lograron el acoplamiento selectivo C-H en superficies de plata, lo que permitió la síntesis de nuevas moléculas orgánicas y cadenas poliméricas. Este avance mejora la química de las superficies más allá de la fabricación tradicional de polímeros.

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Área de la Ciencia:

  • Química de las superficies
  • Síntesis orgánica
  • Nanotecnología

Sus antecedentes:

  • El acoplamiento intermolecular carbono-carbono (C-C) a través de la división de enlaces carbono-halógeno (C-X) es vital para la síntesis de nanoestructuras poliméricas.
  • El acoplamiento C-H no controlado en los carbonos terminales impide la extensión de los polímeros covalentes, limitando su síntesis.
  • El acoplamiento selectivo C-H después de la deshalogenación sigue siendo un área poco explorada en la química de superficies.

Objetivo del estudio:

  • Para investigar el acoplamiento selectivo C-H en diferentes superficies metálicas.
  • Explorar el potencial para sintetizar nuevas moléculas orgánicas y cadenas poliméricas a través de reacciones de acoplamiento controladas.
  • Para avanzar en el campo de la síntesis orgánica asistida por superficie.

Principales métodos:

  • Microscopía de túnel de barrido (STM) para imágenes de superficie de alta resolución.
  • Espectroscopia de fotoelectrones de rayos X (XPS) para el análisis del estado elemental y químico de la superficie.
  • Cálculos de la Teoría Funcional de Densidad (DFT) para comprender los mecanismos de reacción y la energética.

Principales resultados:

  • Se observó un acoplamiento C-C predominante en las superficies de oro (Au) 111.
  • El acoplamiento selectivo C-H se logró en superficies de plata (Ag) 111, un hallazgo novedoso.
  • El acoplamiento selectivo C-H en Ag{111) permitió la síntesis distinta de cadenas poliméricas o nuevas moléculas orgánicas.

Conclusiones:

  • Se ha demostrado un nuevo método para el acoplamiento selectivo de C-H en superficies Ag{111).
  • Este acoplamiento selectivo abre nuevas vías para la síntesis asistida por superficie de moléculas orgánicas complejas.
  • Los hallazgos amplían el alcance de la química de superficies más allá de la fabricación de polímeros in situ.