anti-Carbometalation of Alkynyl Sulfides Using Indium Tribromide and Ketene Silyl Acetals

anti-Carbometalation of Alkynyl Sulfides Using Indium Tribromide and Ketene Silyl Acetals

We developed the regioselective anti-carbometalation of alkynyl sulfides via the use of InBr3 and organosilicon nucleophiles to give β-mercaptoalkenylindium compounds. The structure of β-mercaptoalkenylindium was characterized by X-ray crystallographic analysis. A variety of disubstituted alkenyl su...

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Veröffentlicht in:Chemistry letters 2020-10, Vol.49 (10), p.1136-1139
Hauptverfasser: Kang, Kyoungmin, Sakamoto, Kosuke, Nishimoto, Yoshihiro, Yasuda, Makoto
Format: Artikel
Sprache:eng
Schlagworte:
Acetals
Aromatic compounds
Cross coupling
Crystallography
Halides
Halogenation
Nucleophiles
Sulfides
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Zusammenfassung:We developed the regioselective anti-carbometalation of alkynyl sulfides via the use of InBr3 and organosilicon nucleophiles to give β-mercaptoalkenylindium compounds. The structure of β-mercaptoalkenylindium was characterized by X-ray crystallographic analysis. A variety of disubstituted alkenyl sulfides were regio- and stereoselectively obtained by either halogenation or Pd-catalyzed cross-coupling with aryl halides using the mercaptoalkenylindiums.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.200400