Dearomatization Reactions Using Phthaloyl Peroxide

Dearomatization Reactions Using Phthaloyl Peroxide

A new oxidative dearomatization reaction has been developed using phthaloyl peroxide to chemoselectively install two oxygen–carbon bonds into aromatic precursors. The oxidation reaction proceeds only once; addition of superstoichiometric equivalents of phthaloyl peroxide does not react further with...

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Veröffentlicht in:Organic letters 2015-09, Vol.17 (18), p.4420-4423
Hauptverfasser: Eliasen, Anders M, Christy, Mitchell, Claussen, Karin R, Besandre, Ronald, Thedford, Randal P, Siegel, Dionicio
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container_end_page 4423
container_issue 18
container_start_page 4420
container_title Organic letters
container_volume 17
creator Eliasen, Anders M
Christy, Mitchell
Claussen, Karin R
Besandre, Ronald
Thedford, Randal P
Siegel, Dionicio
description A new oxidative dearomatization reaction has been developed using phthaloyl peroxide to chemoselectively install two oxygen–carbon bonds into aromatic precursors. The oxidation reaction proceeds only once; addition of superstoichiometric equivalents of phthaloyl peroxide does not react further with the newly generated 1,3-cyclohexadiene. The reaction has been challenged by the addition of different functional groups and shown to maintain chemoselectivity. Due to the broad reactivity with 1,2-methylenedioxybenzene derivatives, linear free energy correlations were determined and support a mechanism proceeding through diradicals analogous to arene-hydroxylation reactions using phthaloyl peroxide.
doi_str_mv 10.1021/acs.orglett.5b02008
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title Dearomatization Reactions Using Phthaloyl Peroxide
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