1,2-Bis(arylthio)arene synthesis via aryne intermediates

1,2-Bis(arylthio)arene synthesis via aryne intermediates

Lithium 1,1-diadamantylamide (LDAM) base-promoted insertion of arynes into disulfide S-S bonds is described. After generation of arynes from readily available aryl halides and triflates, reactions with diaryl and diisopropyl disulfides afford the insertion products in moderate to excellent yields. U...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019-08, Vol.55 (64), p.9467-9470
Hauptverfasser: Mesgar, Milad, Nguyen-Le, Justin, Daugulis, Olafs
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic compounds
aromatic hydrocarbons
chemical bonding
chemical reactions
Cyclohexene
cyclohexenes
disulfides
Halides
Insertion
Lithium
organic halogen compounds
organic sulfur compounds
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Zusammenfassung:Lithium 1,1-diadamantylamide (LDAM) base-promoted insertion of arynes into disulfide S-S bonds is described. After generation of arynes from readily available aryl halides and triflates, reactions with diaryl and diisopropyl disulfides afford the insertion products in moderate to excellent yields. Use of 1-cyclohexenyl triflate gave an excellent yield of 1,2-bis(phenylthio)cyclohexene.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c9cc03863a