Annulation of Alkynyl Aryl Ethers with Allyl Pivalates To Give 2,3‐Bismethylenechromanes through Double C−H Bond Cleavage |
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| Authors: | Dr. Yasunori Minami Megumi Sakai Tomohiro Anami Prof. Dr. Tamejiro Hiyama |
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| Affiliation: | 1. Research and Development Initiative, Chuo University, Tokyo, Japan;2. Department of Applied Chemistry, Chuo University, Tokyo, Japan |
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| Abstract: | 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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| Keywords: | alkynes allyl substrates annulation C− C coupling C− H activation |
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