Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes

Andrés Seoane; Noelia Casanova; Noelia Quiñones; José L. Mascareñas; Moisés Gulías

doi:10.1021/ja5034952

Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes

Andrés Seoane, Noelia Casanova, Noelia Quiñones, José L. Mascareñas^*, Moisés Gulías

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Resum

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.

Idioma original	Anglès
Pàgines (de-a)	7607-7610
Nombre de pàgines	4
Revista	Journal of the American Chemical Society
Volum	136
Número	21
DOIs	https://doi.org/10.1021/ja5034952
Estat de la publicació	Publicada - 28 de maig 2014
Publicat externament	Sí

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title = "Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes",

abstract = "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.",

author = "Andr{\'e}s Seoane and Noelia Casanova and Noelia Qui{\~n}ones and Mascare{\~n}as, \{Jos{\'e} L.\} and Mois{\'e}s Gul{\'i}as",

year = "2014",

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doi = "10.1021/ja5034952",

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T1 - Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes

AU - Seoane, Andrés

AU - Casanova, Noelia

AU - Quiñones, Noelia

AU - Mascareñas, José L.

AU - Gulías, Moisés

PY - 2014/5/28

Y1 - 2014/5/28

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84901712977

U2 - 10.1021/ja5034952

DO - 10.1021/ja5034952

M3 - Article

AN - SCOPUS:84901712977

SN - 0002-7863

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 21

ER -

Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes

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