Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement

Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement

The gold­(I)-catalyzed reaction of bromoalkynes with allylsilanes gives 1,4-enynes in a formal cross-coupling reaction. Mechanistic studies revealed the involvement of gold­(I) vinylidenes or vinylidenephenonium gold­(I) cations depending on the substituent on the bromoalkyne. In the case of bromo a...

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Veröffentlicht in:ACS catalysis 2019-09, Vol.9 (9), p.7817-7822
Hauptverfasser: de Orbe, M. Elena, Zanini, Margherita, Quinonero, Ophélie, Echavarren, Antonio M
Format: Artikel
Sprache:eng
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Zusammenfassung:The gold­(I)-catalyzed reaction of bromoalkynes with allylsilanes gives 1,4-enynes in a formal cross-coupling reaction. Mechanistic studies revealed the involvement of gold­(I) vinylidenes or vinylidenephenonium gold­(I) cations depending on the substituent on the bromoalkyne. In the case of bromo arylalkynes, the vinylidenephenonium gold­(I) cations lead to 1,4-enynes via a 1,2-aryl rearrangement. The same reactivity has been observed in the presence of InBr3.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b02314