Straightforward assembly of benzoxepines by means of a rhodium(III)- catalyzed C-H functionalization of o-vinylphenols

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

doi:10.1021/ja410538w

Straightforward assembly of benzoxepines by means of a rhodium(III)- catalyzed C-H functionalization of o-vinylphenols

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

^*Autor corresponent d’aquest treball

Producció científica: Article en revista indexada › Article › Avaluat per experts

238 Cites (Scopus)

Resum

Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl₂] ₂ and Cu(OAc)₂. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

Idioma original	Anglès
Pàgines (de-a)	834-837
Nombre de pàgines	4
Revista	Journal of the American Chemical Society
Volum	136
Número	3
DOIs	https://doi.org/10.1021/ja410538w
Estat de la publicació	Publicada - 22 de gen. 2014
Publicat externament	Sí

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title = "Straightforward assembly of benzoxepines by means of a rhodium(III)- catalyzed C-H functionalization of o-vinylphenols",

abstract = "Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2] 2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.",

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",

month = jan,

day = "22",

doi = "10.1021/ja410538w",

language = "English",

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T1 - Straightforward assembly of benzoxepines by means of a rhodium(III)- catalyzed C-H functionalization of o-vinylphenols

AU - Seoane, Andrés

AU - Casanova, Noelia

AU - Quiñones, Noelia

AU - Mascareñas, José L.

AU - Gulías, Moisés

PY - 2014/1/22

Y1 - 2014/1/22

N2 - Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2] 2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

AB - Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2] 2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

UR - https://www.scopus.com/pages/publications/84892985968

U2 - 10.1021/ja410538w

DO - 10.1021/ja410538w

M3 - Article

AN - SCOPUS:84892985968

SN - 0002-7863

VL - 136

SP - 834

EP - 837

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 3

ER -

Straightforward assembly of benzoxepines by means of a rhodium(III)- catalyzed C-H functionalization of o-vinylphenols

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