Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 30, Pages 8701-8705Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602252
Keywords
alkynes; allyl substrates; annulation; C-C coupling; C-H activation
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Funding
- JST
- ACT-C
- JSPS [25870747]
- Grants-in-Aid for Scientific Research [25870747] Funding Source: KAKEN
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The treatment of silylethynyloxyarenes with allylic pivalates in the presence of a palladium catalyst led to efficient C-H bond cleavage in both substrates and a novel annulation reaction to give 2,3-bismethylenechromanes. When ortho-allylated silylethynyloxybenzenes were used as the substrates, the same products were obtained. This result shows that site-selective intramolecular hydrovinylation is involved in the annulation reaction. The synthetic utility of the products was demonstrated by the construction of condensed polycycles.
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