Pd- and Rh-Catalyzed Hydroarylation of γ-(2-Methoxycarbonylphenyl)propargylic Alcohols: Approaches to 4- or 5-Substituted Seven-Membered Benzolactones and 3,3- Disubstituted Phthalides

Arcadi, Antonio; Fabrizi, G; Goggiamani, A; Marinelli, Fabio

doi:10.1021/acs.joc.5b00663

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A study of the palladium-catalyzed hydroarylation/hydrovinylation reaction of γ-(2-methoxycarbonylphenyl)-propargylic alcohols with aryl iodides/vinyl triflates and of the rhodium-catalyzed one with organoboron derivatives is described.The opposite regiochemical outcome of the two processes allows an easy selective approach to 5- or 4-substituted benzoxepin-1(3H)-ones by combining the hydroarylative/hydrovinylative step with cyclocondensation between −OH and −COOMe groupsin the intermediate γ,γ-disubstituted or β,γ-disubstituted allylic alcohols. A one-flask procedure to give benzo[c]oxepin-1(3H)-ones directly from the starting alkyne has been also developed. Treatment of crude γ,γ-disubstituted allylic alcohols with NaOH, followed by acidification, affords 3,3-disubstituted phthalides.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11697/9691

Titolo:	Pd- and Rh-Catalyzed Hydroarylation of γ-(2-Methoxycarbonylphenyl)propargylic Alcohols: Approaches to 4- or 5-Substituted Seven-Membered Benzolactones and 3,3- Disubstituted Phthalides
Autori:	ARCADI, Antonio [Membro del Collaboration Group] Fabrizi G [Membro del Collaboration Group] Goggiamani A [Membro del Collaboration Group] MARINELLI, Fabio [Writing – Original Draft Preparation] (Corresponding) mostra contributor esterni nascondi contributor esterni
Data di pubblicazione:	2015
Rivista:	JOURNAL OF ORGANIC CHEMISTRY
Abstract:	A study of the palladium-catalyzed hydroarylation/hydrovinylation reaction of γ-(2-methoxycarbonylphenyl)-propargylic alcohols with aryl iodides/vinyl triflates and of the rhodium-catalyzed one with organoboron derivatives is described.The opposite regiochemical outcome of the two processes allows an easy selective approach to 5- or 4-substituted benzoxepin-1(3H)-ones by combining the hydroarylative/hydrovinylative step with cyclocondensation between −OH and −COOMe groupsin the intermediate γ,γ-disubstituted or β,γ-disubstituted allylic alcohols. A one-flask procedure to give benzo[c]oxepin-1(3H)-ones directly from the starting alkyne has been also developed. Treatment of crude γ,γ-disubstituted allylic alcohols with NaOH, followed by acidification, affords 3,3-disubstituted phthalides.
Handle:	http://hdl.handle.net/11697/9691
Appare nelle tipologie:	1.1 Articolo in rivista

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