Related Experiment Video
Updated: May 24, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Palladium-Catalyzed C(O)-C Bond Cleavage of Unstrained Ketones Assisted with Aryl Handles: An Approach to Diaryl
Qiang Li1, Yang Long2, Qinyue Tao1
1College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Abstract:
C-C bond cleavage reactions have achieved remarkable progress in molecular deconstruction and skeleton editing. In this study, we describe a palladium-catalyzed synthesis of diaryl ketones through a sequence of α-arylation and aerobic oxidative C-C bond cleavage. This transformation features good functional group compatibility, especially for highly reactive groups, including -OH, NH2, and -CHO. Furthermore, this approach allows for gram-scale synthesis in a low catalyst loading manner. It also streamlines the synthesis of a variety of drugs or their intermediates. Mechanism studies reveal the essential role of utilizing a bulky ligand and the existence of air as the reaction atmosphere.
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Related Concept Videos
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
Alkynes to Carboxylic Acids: Oxidative Cleavage
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.
α-Alkylation of Ketones via Enolate Ions
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
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...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction