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Updated: Nov 17, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Diverse diaryl sulfide synthesis through consecutive aryne reactions
Hana Nakajima1, Yuki Hazama1, Yuki Sakata1
1Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan. s-yoshida.cb@tmd.ac.jp.
Synthesize diverse diaryl sulfides efficiently using a novel demethylative hydrothiolation method. This approach utilizes aryne intermediates for broad structural applicability in organic synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Diaryl sulfides are important structural motifs in pharmaceuticals and materials science.
- Existing synthetic methods for diaryl sulfides often lack efficiency or structural diversity.
Purpose of the Study:
- To develop an efficient and versatile method for synthesizing structurally diverse diaryl sulfides.
Main Methods:
- Generation of aryne intermediates from o-iodoaryl triflates.
- Demethylative hydrothiolation using methylthio-substituted o-silylaryl triflates.
- Subsequent aryne reactions to form diaryl sulfides.
Main Results:
- Successful synthesis of a wide range of diaryl sulfides.
- Demonstrated efficiency and structural diversity of the developed method.
- The reaction proceeds through a demethylative hydrothiolation pathway.
Conclusions:
- The novel method provides an efficient route to structurally diverse diaryl sulfides.
- This approach offers a valuable tool for organic synthesis and medicinal chemistry.
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