Related Experiment Video
Updated: Jan 24, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Utilizing Native Directing Groups: Mechanistic Understanding of a Direct Arylation Leads to Formation of Tetracyclic
Steven R Wisniewski1, Scott A Savage1, Evan O Romero1
1Chemical and Synthetic Development , Bristol-Myers Squibb , One Squibb Drive, New Brunswick , New Jersey 08903 , United States.
Abstract:
A mechanistic study on a direct arylation using a native picolylamine directing group is reported. Kinetic studies determined the concentration dependence of substrates and catalysts, as well as catalyst degradation, which led to the development of a new set of reaction conditions capable of affording a robust kinetic profile. During reaction optimization, a small impurity was observed, which was determined to be a dual C-H activation product. A second set of conditions were found to flip the selectivity of the C-H activation to form this tetracycle in high yield. A catalytic cycle is proposed for the intermolecular/intramolecular C-H activation pathway.
More Related Videos
Related Concept Videos
Intermolecular vs Intramolecular Forces
Nomenclature of Aryl and Heterocyclic Amines
Radical Reactivity: Intramolecular vs Intermolecular
Intermolecular Forces
Directing Effect of Substituents: meta-Directing Groups
Intermolecular Forces in Solutions
When the strengths of the intermolecular forces of attraction between solute and solvent species in a solution are no different than those present in the separated components, the solution is formed with no accompanying energy change. Such a solution is called an ideal solution. A mixture of ideal gases (or gases such as helium and argon,...

