Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes | Zendy

Andrés Seoane | Zendy; Noelia Casanova | Zendy; Noelia Quiñones | Zendy; José L. Mascareñas | Zendy; Moisés Gulı́as | Zendy

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Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes

Author(s) -

Andrés Seoane,

Noelia Casanova,

Noelia Quiñones,

José L. Mascareñas,

Moisés Gulı́as

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5034952

Subject(s) - chemistry , annulation , moiety , catalysis , cycloaddition , rhodium , selectivity , cleavage (geology) , bond cleavage , phenol , ring (chemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering

Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.

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