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Annulation of Alkynyl Aryl Ethers with Allyl Pivalates To Give 2,3-Bismethylenechromanes through Double C-H Bond Cleavage



Annulation of Alkynyl Aryl Ethers with Allyl Pivalates To Give 2,3-Bismethylenechromanes through Double C-H Bond Cleavage



Angewandte Chemie 55(30): 8701-8705



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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Accession: 057202439

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PMID: 27385632

DOI: 10.1002/anie.201602252


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