Related Experiment Video
Updated: Jan 21, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Nickel-Catalyzed [5+2] Cycloaddition of 10π-Electron Aromatic Benzothiophenes with Alkynes To Form Thermally
Tasuku Inami1, Toshifumi Takahashi1, Takuya Kurahashi1
1Department of Material Chemistry, Graduate School of Engineering , Kyoto University , Kyoto 615-8510 , Japan.
Abstract:
The nickel-catalyzed formal [5+2] cycloaddition of five-membered benzothiophenes and alkynes giving seven-membered benzothiepines via unprecedented dearomatization is reported. The reaction involves the carbothiolation of alkynes with sulfur-containing aromatic heterocycles affording sulfur-containing heterocyclic compounds via ring expansion. As a result, this method facilitates divergent access to thermally metastable benzothiepines. The structure of the thianickelacycle intermediate, which is formed via oxidative addition of the C-S bond in benzothiophenes to nickel(0), was confirmed by in situ X-ray absorption fine structure spectroscopy and density functional theory calculation.
More Related Videos
08:13Chemical Precipitation Method for the Synthesis of Nb2O5 Modified Bulk Nickel Catalysts with High Specific Surface Area
Published on: February 19, 2018
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Electron Carriers
Over the many stages of cellular respiration, glucose breaks down into carbon dioxide and water. Electron carriers pick up electrons lost by glucose in these reactions, temporarily storing and releasing them into the electron...
Electron Affinity
Electron Behavior
Electrons are negatively charged subatomic particles that are attracted to an orbit around the positively-charged nucleus of an atom. They reside in locations that are associated with energy levels called shells and are further organized into sub-shells and orbitals within each shell.
Electrons Orbit the Nucleus
Electrons are found in specific locations outside of the nucleus. The shell in which an electron resides indicates the general energy level of the electron: those closer to the...
Electron Configuration of Multielectron Atoms
Electron Transport Chains
The ETC is comprised of...
Ionic Bonding and Electron Transfer