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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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Halogens03:01

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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
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Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Bonding in Metals

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Halogen Bond Catalyzed Bromocarbocyclization.

Yuk-Cheung Chan1, Ying-Yeung Yeung1

  • 1Department of Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China.

Angewandte Chemie (International Ed. in English)
|February 10, 2018
PubMed
Summary
This summary is machine-generated.

A novel halogen-bonding organocatalyst enables chemoselective bromo-carbocyclization of cinnamyl derivatives. This groundbreaking method demonstrates the first organocatalyst-promoted electrophilic halogenation, revealing an autocatalytic mechanism.

Keywords:
cyclizationhalogensheterocyclesorganocatalysisreaction mechanisms

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Halogen Bonding

Background:

  • Electrophilic halogenation is a crucial synthetic tool.
  • Organocatalysis offers sustainable alternatives to metal catalysis.
  • Halogen bonding is an emerging non-covalent interaction in catalysis.

Purpose of the Study:

  • To develop a novel halogen bond catalyzed bromo-carbocyclization reaction.
  • To demonstrate the first use of a halogen-bonding organocatalyst for electrophilic halogenation.
  • To investigate the reaction mechanism and chemoselectivity.

Main Methods:

  • Utilized N-methyl 4-iodopyridinium triflate as a halogen-bonding organocatalyst.
  • Performed bromo-carbocyclization of N-cinnamyl sulfonamides and O-cinnamyl phenyl ethers.
  • Conducted mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Achieved highly chemoselective bromo-carbocyclization.
  • Demonstrated proof-of-concept for halogen-bonding organocatalyst-promoted electrophilic halogenation.
  • Identified an autocatalytic nature of the reaction through mechanistic studies.

Conclusions:

  • Developed an efficient and selective halogen bond catalyzed bromo-carbocyclization.
  • Established a new paradigm for organocatalyst-promoted electrophilic halogenation.
  • The reaction proceeds via an autocatalytic pathway, offering potential for further optimization.