期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 359, 期 2, 页码 225-233出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600987
关键词
diynes; dual activation; fluorenes; gold catalysis; gold vinylidenes
资金
- RISE programme of the ACS
- DAAD
1,5-Diyne systems bearing one terminal and one benzyl-or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp(2))-H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield.
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