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Rhodium‐Catalyzed (5+1) Annulations Between 2‐Alkenylphenols and Allenes: A Practical Entry to 2,2‐Disubstituted 2H‐Chromenes
Authors:Noelia Casanova  Andrés Seoane  Prof. José L. Mascareñas  Dr. Moisés Gulías
Affiliation:Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica 15782. Universidade de Santiago de Compostela (Spain)
Abstract: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 C? H 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 C? C coupling followed by two sequential pericyclic processes.
Keywords:allenes  annulations  C  H activation  reaction mechanisms  rhodium
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