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 groups in 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.

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, Giancarlo; Goggiamani, Antonella; Marinelli, Fabio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:14(2015), pp. 6986-6995. [10.1021/acs.joc.5b00663]

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

FABRIZI, Giancarlo;GOGGIAMANI, ANTONELLA;
2015

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 groups in 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.
alkynes; benzofurans; catalysis; lactones; molecular structure; palladium; propanols; rhodium; organic chemistry; medicine (all)
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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, Giancarlo; Goggiamani, Antonella; Marinelli, Fabio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:14(2015), pp. 6986-6995. [10.1021/acs.joc.5b00663]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/867568
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