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Review
. 2009 Dec 16;14(12):5308-22.
doi: 10.3390/molecules14125308.

Molecular iodine--an expedient reagent for oxidative aromatization reactions of alpha,beta-unsaturated cyclic compounds

Malose Jack Mphahlele  1
Affiliations
Review

Molecular iodine--an expedient reagent for oxidative aromatization reactions of alpha,beta-unsaturated cyclic compounds

Malose Jack Mphahlele. Molecules. .

Abstract

Prompted by the scant attention paid by published literature reviews to the applications of molecular iodine in oxidative aromatization reactions, we decided to review methods developed to-date involving iodine as an oxidant to promote aromatization of alpha,beta-unsaturated cyclic compounds.

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Figures

Figure 1
Figure 1
Structures of olivetol 1a and DB2073 1b.
Figure 2
Figure 2
Structures of naturally occurring 2-aryl-4-methoxyquinolines.
Scheme 1
Scheme 1
Iodine-promoted oxidative aromatization of Hagemann’s esters.
Scheme 2
Scheme 2
Iodine-promoted oxidative aromatization of cyclohexane-1,3-diones to anisole derivatives.
Scheme 3
Scheme 3
Iodine-promoted oxidative aromatization of 3-phosphonomethylcyclohexenones.
Scheme 4
Scheme 4
Iodine-mediated aromatization of diethyl 1-(1-hydroxy-3-methylcyclohex-2-enyl)alkylphosphonates.
Scheme 5
Scheme 5
Iodine-mediated aromatization of ketophosphonates 15.
Scheme 6
Scheme 6
Iodine-methanol–mediated aromatization of dihydrofuran derivative 11.
Scheme 7
Scheme 7
Iodine-methanol–mediated aromatization of cyclic diones.
Scheme 8
Scheme 8
Iodine-mediated aromatization of 2-halogenomethyl-3,5,6,7-tetrahydrobenzofuran-4-ones.
Scheme 9
Scheme 9
Iodine-mediated aromatization of 3-bromo-2,3,4,6,7,8-hexahydro-1-benzopyran-5-ones.
Scheme 10
Scheme 10
Iodine-promoted oxidative aromatization of 2-acyl- and 2-propionylcyclohexane-1,3-diones.
Scheme 11
Scheme 11
Iodine-methanol oxidative aromatization of benzo[b]indeno[2.1-d]furanone derivatives.
Scheme 12
Scheme 12
Iodine-methanol promoted oxidative aromatization of 4-alkylidene-2-cyclohexen-1-ones.
Scheme 13
Scheme 13
Iodine-CAN promoted oxidative aromatization of trimethyl-2-cyclohexen-1-ones.
Scheme 14
Scheme 14
Iodine-promoted oxidative aromatization of 2-aryl-1,2,3,4-tetrahydroquinolin-4-ones.
Scheme 15
Scheme 15
Iodine-sodium ethoxide–promoted aromatization of 2-cyclohexenone-4-carboxylates.
Scheme 16
Scheme 16
Iodine-sodium ethoxide–promoted aromatization of enamine derivatives.
Scheme 17
Scheme 17
Iodine-promoted aromatization of 1,4-dihydropyridines under neutral and ultrasonic irradiation conditions.
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