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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

7.2K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.3K
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

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.1K
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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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

4.1K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Related Experiment Video

Updated: Mar 13, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Platinum-Catalyzed C-H Functionalization.

Jay A Labinger1

  • 1Beckman Institute, California Institute of Technology , Pasadena, California 91125, United States.

Chemical Reviews
|October 22, 2016
PubMed
Summary

Platinum complexes enable C-H bond activation and functionalization, covering mechanistic studies, stoichiometric reactions, and catalytic bond formations (C-O, C-C, C-B). This survey highlights current trends and future opportunities in platinum-catalyzed C-H activation.

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • C-H bond activation is a key challenge in chemistry.
  • Platinum complexes offer unique reactivity for C-H functionalization.

Purpose of the Study:

  • To survey recent advancements in C-H activation and functionalization using platinum complexes.
  • To discuss mechanistic insights, reaction types, and future trends in the field.

Main Methods:

  • Review of fundamental mechanistic investigations.
  • Analysis of stoichiometric and catalytic reactions.
  • Examination of reactions involving dioxygen and Pt(II) complexes.

Main Results:

  • Detailed overview of intra- and intermolecular C-H activation by Pt complexes.

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  • Exploration of Pt-mediated C-O, C-C, and C-B bond formation.
  • Discussion of Pt(II) complex reactions relevant to substrate oxygenation.

    • Conclusions:

    • Platinum complexes are versatile catalysts for C-H activation and functionalization.
    • Significant progress has been made in understanding mechanisms and expanding reaction scope.
    • Future research opportunities lie in developing novel catalytic systems and applications.