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Halogenation of Alkenes02:46

Halogenation of Alkenes

16.9K
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.
16.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.7K
Alkyl Halides02:45

Alkyl Halides

17.8K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
17.8K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.9K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.9K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.0K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.0K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.6K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.6K

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Are bis(pyridine)iodine(I) complexes applicable for asymmetric halogenation?

Daniel von der Heiden1, Flóra Boróka Németh2, Måns Andreasson3

  • 1Department of Chemistry - BMC, Uppsala University, SE-751 23 Uppsala, Sweden. mate.erdelyi@kemi.uu.se.

Organic & Biomolecular Chemistry
|September 15, 2021
PubMed
Summary

Chiral iodine(I) complexes show efficient iodenium transfer to alkenes but lack enantioselectivity. Achieving stereoselective halofunctionalization requires catalyst-induced substrate preorganization.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis

Background:

  • Enantiopure halogenated molecules are crucial synthetic intermediates.
  • Enantioselective halofunctionalization methods are underdeveloped.

Purpose of the Study:

  • To explore chiral trans-chelating bis(pyridine)iodine(I) complexes for catalytic enantioselective halofunctionalization.
  • To design and synthesize novel chiral bidentate pyridine donor ligands and their iodine(I) complexes.

Main Methods:

  • Synthesis of six novel chiral bidentate pyridine donor ligands.
  • Formation and characterization of [N-I-N]+-type halogen bond complexes using 15N NMR and DFT.
  • Investigation of iodenium transfer to alkenes.

Main Results:

  • Chiral iodine(I) complexes facilitated efficient iodenium transfer to alkenes.
  • The developed complexes did not provide enantioselectivity in the halofunctionalization reactions.
  • Multiple ligand conformations and insufficient steric hindrance were identified as reasons for the lack of stereoselectivity.

Conclusions:

  • Substrate preorganization by the chiral catalyst is necessary for enantioselective halofunctionalization.
  • Current chiral bis(pyridine)iodine(I) complexes are not suitable for enantioselective halofunctionalization without modification.