Umpolung Reactivity of Indole through Gold Catalysis

Umpolung Reactivity of Indole through Gold Catalysis

Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho‐azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophil...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-08, Vol.50 (36), p.8358-8362
Hauptverfasser: Lu, Biao, Luo, Yingdong, Liu, Lianzhu, Ye, Longwu, Wang, Yanzhao, Zhang, Liming
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Catalysis
gold
Gold - chemistry
Imines - chemistry
indole
Indoles - chemistry
Methane - analogs & derivatives
Methane - chemistry
nitrenes
Stereoisomerism
umpolung
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Zusammenfassung:Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho‐azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3‐position. A range of functionalized indoles is readily accessed by utilizing this strategy.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201103014