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Combining Gold(I)/Gold(III) Catalysis and CH Functionalization: A Formal Intramolecular [3+2] Annulation towards Tricyclic Indolines and Mechanistic Studies
Author(s) -
Zhang Guozhu,
Luo Yingdong,
Wang Yanzhao,
Zhang Liming
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100293
Subject(s) - intramolecular force , selectfluor , moiety , annulation , octane , chemistry , combinatorial chemistry , tetrafluoroborate , catalysis , surface modification , aniline , medicinal chemistry , organic chemistry , ionic liquid
Gold rush : A combination of oxidative gold(I)/gold(III) catalysis and CH functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2H 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)].