Related Experiment Video
Updated: Oct 15, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
2-(Chlorodiisopropylsilyl)-6-(trimethylsilyl)phenyl triflate: a modified platform for intramolecular benzyne
Tsukasa Tawatari1, Kiyosei Takasu1, Hiroshi Takikawa1
1Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. kay-t@pharm.kyoto-u.ac.jp.
Abstract:
2-(Chlorodiisopropylsilyl)-6-(trimethylsilyl)phenyl triflate serves as an efficient aryne precursor for intramolecular benzyne [4 + 2] or (2 + 2 + 2) cycloadditions. Key features of this precursor are (1) rapid connection of various arynophiles to the precursor via a Si-O bond and (2) generation of aryne under mild conditions using a combination of Cs2CO3 and 18-crown-6.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Reactions at the Benzylic Position: Halogenation
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Hydrolysis of Chlorobenzene to Phenol: Dow Process