Combining Gold(I)/Gold(III) Catalysis and CH Functionalization: A Formal Intramolecular [3+2] Annulation towards Tricyclic Indolines and Mechanistic Studies

Combining Gold(I)/Gold(III) Catalysis and CH Functionalization: A Formal Intramolecular [3+2] Annulation towards Tricyclic Indolines and Mechanistic Studies

Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and CH functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiet...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-05, Vol.50 (19), p.4450-4454
Hauptverfasser: Zhang, Guozhu, Luo, Yingdong, Wang, Yanzhao, Zhang, Liming
Format: Artikel
Sprache:eng
Schlagworte:
gold
homogeneous catalysis
nitrogen heterocycles
oxidation
reaction mechanisms
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Zusammenfassung:Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and CH functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiety [see scheme; Tf=trifluoromethanesulfonyl, Selectfluor=1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)].
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100293