Metal- and solvent-free direct C-H thiolation of aromatic compounds with sulfonyl chlorides

A simple, efficient and green method for the direct thiolation of aromatic compounds using commercially available sulfonyl chlorides as the sulfur source was developed under metal- and solvent-free conditions. The C-S bond was constructed via direct C-H functionalization of diverse aromatic compound...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2020, Vol.22 (2), p.427-432
Hauptverfasser: Zhao, Feng, Tan, Qi, Wang, Dahan, Deng, Guo-Jun
Format: Artikel
Sprache:eng
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Zusammenfassung:A simple, efficient and green method for the direct thiolation of aromatic compounds using commercially available sulfonyl chlorides as the sulfur source was developed under metal- and solvent-free conditions. The C-S bond was constructed via direct C-H functionalization of diverse aromatic compounds under an oxygen atmosphere. In this process, various diaryl sulfides were synthesized in moderate to excellent yields. This protocol shows a broad substrate scope and good functional group tolerance. Moreover, a gram-scale experiment was also conducted to prove the prospect of this method for the scale-up synthesis of diaryl sulfides. Mechanistic studies indicate that this procedure probably undergoes a radical pathway. A simple method for the direct thiolation of aromatic compounds using sulfonyl chlorides was developed under metal- and solvent-free conditions.
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc03384j