Related Experiment Video
Updated: Oct 17, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Reppe-Type Regioselective Assembly of Meta-Teraryls using Phenyl Vinyl Sulfone as a Traceless Acetylene Surrogate
Stephen M Long1, Emily L Heller1, Cody A Tolliver1
1C. Eugene Bennett Department of Chemistry, West Virginia University, PO Box 6201, Morgantown, West Virginia 26506, United States.
Abstract:
Benzene rings are among the most frequently encountered ring systems in small-molecule drugs, but only a few substitution patterns (1-, 1,2-, 1,4-, and 1,2,4-) predominate. Here, regioselective nickel-catalyzed three-component cyclotrimerization of terminal alkynes and phenyl vinyl sulfone was used to synthesize an underrepresented substitution pattern, the 1,3-arene. Phenyl vinyl sulfone serves as an acetylene surrogate for the regiocontrolled synthesis of meta-terphenyl derivatives. The reaction demonstrated wide functional group tolerance with moderate to good yields. Stoichiometric reactivity studies with catalytically relevant nickel complexes established the mechanistic origin of the observed regioselectivity.
More Related Videos
Related Concept Videos
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Cycloaddition Reactions: Overview
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

