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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

21.4K
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.
21.4K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.4K
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...
4.4K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.3K
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...
5.3K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

12.2K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
12.2K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

4.0K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
4.0K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

13.1K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
13.1K

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Related Experiment Video

Updated: Apr 11, 2026

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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Manganese Catalyzed C-H Halogenation.

Wei Liu1, John T Groves1

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Accounts of Chemical Research
|June 5, 2015
PubMed
Summary

Manganese porphyrins catalyze new C-H bond formations, including direct fluorination using simple fluoride salts. This breakthrough enables late-stage drug labeling for PET imaging via Heteroatom-Rebound Catalysis (HRC).

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Cytochrome P450 enzymes catalyze aliphatic C-H hydroxylations, inspiring synthetic models.
  • Manganese porphyrins mimic P450 reactivity, particularly in alkane hydroxylation and olefin epoxidation.
  • Previous manganese porphyrin applications were limited to oxygenation due to rapid oxygen transfer.

Purpose of the Study:

  • To develop novel manganese porphyrin-catalyzed carbon-halogen bond formations.
  • To explore direct aliphatic C-H fluorination reactions.
  • To enable late-stage radiolabeling of drug molecules for PET imaging.

Main Methods:

  • Utilized biphasic sodium hypochlorite/manganese porphyrin systems for C-Cl bond formation.
  • Investigated manganese porphyrin-catalyzed direct C-H fluorination using nucleophilic fluoride salts.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Last Updated: Apr 11, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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  • Employed mechanistic studies, DFT calculations, and radical clock experiments (norcarane oxidation).

    • Main Results:

    • Developed efficient and selective conversion of unactivated aliphatic C-H bonds to C-Cl bonds.
    • Discovered the first Mn-catalyzed direct aliphatic C-H fluorination reactions.
    • Identified a trans-difluoromanganese(IV) species as the key fluorine transfer intermediate.
    • Enabled radioactive (18)F fluorine incorporation via C-H activation using manganese salen complexes.
    • Achieved the first direct Csp(3)-H bond (18)F labeling with no-carrier-added [(18)F]fluoride.

    Conclusions:

    • Manganese porphyrins and salen complexes can catalyze novel carbon-heteroatom bond formations beyond oxygenation.
    • The developed Heteroatom-Rebound Catalysis (HRC) strategy offers a versatile tool for C-H functionalization.
    • This approach facilitates late-stage labeling of drug molecules for PET imaging, enhancing diagnostic capabilities.