Related Experiment Video
Updated: Feb 26, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed Transformations of Alkyl C-H Bonds
Jian He1, Masayuki Wasa1, Kelvin S L Chan1
1Department of Chemistry, The Scripps Research Institute , 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
This review covers advances in palladium-catalyzed C(sp3)-H activation using different oxidation states. Directing group strategies and ligands are key for selective C-C and C-heteroatom bond formation in synthetic chemistry.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Chemistry
Background:
- Palladium-catalyzed C-H activation is a powerful tool in organic synthesis.
- Controlling regioselectivity and reactivity in C(sp3)-H activation remains a challenge.
Purpose of the Study:
- To summarize recent advancements in palladium-catalyzed C(sp3)-H activation.
- To highlight the role of various redox manifolds and directing group strategies.
- To discuss the impact of ligands on reactivity and selectivity.
Main Methods:
- Review of literature on Pd-catalyzed C(sp3)-H activation.
- Analysis of different redox cycles (Pd(0)/Pd(II), Pd(II)/Pd(IV), Pd(II)/Pd(0)).
- Examination of directing group strategies for regiocontrol.
- Evaluation of mono- and bidentate ligands for enhanced reactivity and selectivity.
Main Results:
- Significant progress in C(sp3)-H activation across various redox states.
- Development of numerous C-C and C-heteroatom bond-forming reactions using directing groups.
- Demonstration of ligands' effectiveness in controlling reactivity and enantioselectivity.
- Limited examples in alkane C-H bond activation, but broad applicability in functionalization.
Conclusions:
- Palladium-catalyzed C(sp3)-H activation has advanced significantly.
- Directing group strategies and tailored ligands are crucial for selective functionalization.
- This field offers substantial opportunities for developing novel synthetic methodologies.
More Related Videos
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
06:26Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
Published on: August 17, 2018
Related Concept Videos
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
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...
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
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 reactions,...