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Cycloisomerization of Aromatic Homo- and Bis-homopropargylic Alcohols via Catalytic Ru Vinylidenes: Formation of Benzofurans and Isochromenes

Alejandro Varela-Fernández, Carlos González-Rodríguez, Jesús A. Varela, Luis Castedo and Carlos Saá*

*Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Email: carlos.saausc.es

A. Varela-Fernández, C. González-Rodríguez, J. A. Varela, L. Castedo, Carlos Saá, Org. Lett., 2009, 11, 5350-5353.

DOI: 10.1021/ol902212h (free Supporting Information)



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Abstract

An effective, Ru-catalyzed cycloisomerization of benzannulated homo- and bis-homopropargylic alcohols affords benzofurans and isochromenes chemo- and regioselectively (5-, and 6-endo cyclizations). The presence of an amine/ammonium base-acid pair is crucial for the catalytic cycle.

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Key Words

Benzofurans, Isochromenes


ID: J54-Y2009-3390