Thiolate-Initiated Synthesis of Dibenzothiophenes from 2,2'-Bis(methylthio)-1,1'-Biaryl Derivatives through Cleavage of Two Carbon-Sulfur Bonds
Yoshihiro Masuya, Yuki Kawashima, Takuya Kodama, Naoto Chatani*, Mamoru Tobisu*
*Department of Applied Chemistry, Graduate School of
Engineering, Osaka University, Suita, Osaka 565-0871, Japan,
Email: chatani
chem.eng.osaka-u.ac.jp, tobisuchem.eng.osaka-u.ac.jp
Y. Masuya, Y. Kawashima, T. Kodama, N. Chatani, M. Tobisu, Synlett, 2019, 30, 1995-1999.
DOI: 10.1055/s-0037-1611974
see article for more reactions
Abstract
A thiolate anion promotes a transition-metal free cleavage of two carbon-sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives. The subsequent dibenzothiophene-forming cyclization step proceeds through a concerted nucleophilic aromatic substitution (CSNAr) mechanism.
see article for more examples
While ads financed 62% of the published abstracts in 2024, donations allowed us to publish additional 12%. 26% of the abstracts have been published voluntarly. If you kindly donate, we can publish more freely accessible information and help the chemical community even more:
If you don't like pawalls or a flood of more and more advertising, then you can send a clear signal here!
Key Words
C-S cleavage, C-O cleavage, metathesis, benzo-fused S-heterocycles
ID: J72-Y2019
