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: chatanichem.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

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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 (CS_NAr) mechanism.

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Key Words

C-S cleavage, C-O cleavage, metathesis, benzo-fused S-heterocycles

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ID: J72-Y2019