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Annulation of Alkynyl Aryl Ethers with Allyl Pivalates To Give 2,3‐Bismethylenechromanes through Double C−H Bond Cleavage
Author(s) -
Minami Yasunori,
Sakai Megumi,
Anami Tomohiro,
Hiyama Tamejiro
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602252
Subject(s) - annulation , chemistry , intramolecular force , cleavage (geology) , allylic rearrangement , aryl , catalysis , bond cleavage , palladium , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , alkyl , fracture (geology) , composite material
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.