Novel highly regioselective VO(acac)2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones

Lattanzi, A.; Senatore, A.; Massa, A.; Scettri, A.

doi:10.1021/jo026783j

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A novel mild methodology for the preparation of o-hydroxybenzyl ketones is described starting from o-alkenyl phenols and based on the VO(acac)(2)/TBHP (2 mol %/1.2 equiv) system. VO(acac)(2) first catalyzes the epoxidation of o-alkenyl phenols and then the rearrangement of the epoxyphenols to ketones via the selective benzylic C-O cleavage and 1,2 hydride migration. The protocol has also been applied to set up a useful and easy one-pot conversion of o-alkenyl phenols to benzo[b]furans by means of the sequential addition of TFA, after the generation of the intermediate o-hydroxybenzyl ketones.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/1060500

Titolo:	Novel highly regioselective VO(acac)2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones
Autori interni:	LATTANZI, Alessandra MASSA, Antonio SCETTRI, Arrigo
Data di pubblicazione:	2003
Rivista:	JOURNAL OF ORGANIC CHEMISTRY
Abstract:	A novel mild methodology for the preparation of o-hydroxybenzyl ketones is described starting from o-alkenyl phenols and based on the VO(acac)(2)/TBHP (2 mol %/1.2 equiv) system. VO(acac)(2) first catalyzes the epoxidation of o-alkenyl phenols and then the rearrangement of the epoxyphenols to ketones via the selective benzylic C-O cleavage and 1,2 hydride migration. The protocol has also been applied to set up a useful and easy one-pot conversion of o-alkenyl phenols to benzo[b]furans by means of the sequential addition of TFA, after the generation of the intermediate o-hydroxybenzyl ketones.
Handle:	http://hdl.handle.net/11386/1060500
Appare nelle tipologie:	1.1.2 Articolo su rivista con ISSN

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