期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 1, 页码 31-34出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja2091992
关键词
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资金
- NIH [R01 GM084254]
- National Center for Supercomputing Applications
- NSF [CHE100123]
- UCSB
Facile cycloisomerization of (2-ethynyl-phenyl)alkynes is proposed to be promoted synergistically by two molecules of BrettPhosAuNTf(2), affording tricyclic indenes in mostly good yields. A gold vinylidene is most likely generated as one of the reaction intermediates on the basis of both mechanistic studies and theoretical calculations. Different from the well-known Rh, Ru, and W counterparts, this novel gold species is highly reactive and undergoes facile intramolecular C(sp(3))-H insertions as well as O-H and N-H insertions. The formation step for the gold vinylidene is predicted theoretically to be complex with a bifurcated reaction pathway. A pyridine N-oxide acts as a weak base to facilitate the formation of an alkynylgold intermediate, and the bulky BrettPhos ligand in the gold catalyst likely plays a role in sterically steering the reaction toward formation of the gold vinylidene.
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