Related Experiment Video
Updated: Jul 17, 2025

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
Published on: August 17, 2018
Rhodium(i)-catalyzed cascade C(sp2)-H bond alkylation - amidation of anilines: phosphorus as traceless directing
Marie Peng1, Denis Ari1, Thierry Roisnel1
1Univ. Rennes, CNRS UMR6226 Rennes F-3500 France.
Abstract:
We introduce a versatile Rh(i)-catalyzed cascade reaction, combining C(sp2)-H bond functionalization and amidation between N-arylphosphanamines and acrylates. This innovative approach enables the rapid synthesis of dihydroquinolinone scaffolds, a common heterocycle found in various pharmaceuticals. Notably, the presence of the phosphorus atom facilitates the aniline ortho-C(sp2)-H bond activation prior to N-P bond hydrolysis, streamlining one-pot intramolecular amidation. Moreover, we demonstrate the applicability of this reaction by synthesizing an antipsychotic drug. Detailed mechanistic investigations revealed the involvement of a Rh-H intermediate, with substrate inhibition through catalyst saturation.
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
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Related Concept Videos
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Electrophilic Addition to Alkynes: Hydrohalogenation
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.
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3