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Rhodium‐Catalyzed (5+1) Annulations Between 2‐Alkenylphenols and Allenes: A Practical Entry to 2,2‐Disubstituted 2 H ‐Chromenes
Author(s) -
Casanova Noelia,
Seoane Andrés,
Mascareñas José L.,
Gulías Moisés
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410350
Subject(s) - allene , rhodium , pericyclic reaction , chemistry , moiety , cycloaddition , catalysis , bond cleavage , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
Readily available alkenylphenols react with allenes under rhodium catalysis to provide valuable 2,2‐disubstituted 2H‐chromenes. The whole process, which involves the cleavage of one CH bond of the alkenyl moiety and the participation of the allene as a one‐carbon cycloaddition partner, can be considered a simple, versatile, and atom‐economical (5+1) heteroannulation. The reaction tolerates a broad range of substituents both in the alkenylphenol and in the allene, and most probably proceeds through a mechanism involving a rhodium‐catalyzed CC coupling followed by two sequential pericyclic processes.