2000
DOI: 10.1021/jo9913457
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Chemoselective C−H Oxidation of Alcohols to Carbonyl Compounds with Iodosobenzene Catalyzed by (Salen)chromium Complex

Abstract: Primary and secondary alcohols with benzylically and allylically activated C-H bonds are chemoselectively oxidized to the corresponding carbonyl compounds by the (salen)Cr(III) complex I as the catalyst and iodosobenzene as the oxygen source; the oxidizing species is the Cr(V) oxo complex. Allylic alcohols with fully substituted double bonds give appreciable amounts of epoxides besides the C-H oxidation products enones, while saturated alcohols are less readily oxidized.

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Cited by 86 publications
(51 citation statements)
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“…High chemoselec-cycloalkenols of varying ring size and cyclohexene derivativity is observed in MTO-catalysed sulfoxidations and tives, which bear alkyl or hydroxy functionalities in the alSiϪH insertions; [3] regioselectivity is displayed in the oxi-lylic position, were studied. The observed selectivities were dation of geraniol, [4] which is oxidised preferentially to the compared to those of the reported stoichiometric oxidants 6,7-epoxide rather than to the 3,4-epoxide, and in the oxi-m-CPBA and DMD in order to deduce a likely dihedral dation of 2-methylnaphthalene to Vitamin K 3 . [5] The regio-angle and therewith a plausible transition-state geometry.…”
Section: Introductionmentioning
confidence: 88%
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“…High chemoselec-cycloalkenols of varying ring size and cyclohexene derivativity is observed in MTO-catalysed sulfoxidations and tives, which bear alkyl or hydroxy functionalities in the alSiϪH insertions; [3] regioselectivity is displayed in the oxi-lylic position, were studied. The observed selectivities were dation of geraniol, [4] which is oxidised preferentially to the compared to those of the reported stoichiometric oxidants 6,7-epoxide rather than to the 3,4-epoxide, and in the oxi-m-CPBA and DMD in order to deduce a likely dihedral dation of 2-methylnaphthalene to Vitamin K 3 . [5] The regio-angle and therewith a plausible transition-state geometry.…”
Section: Introductionmentioning
confidence: 88%
“…and diastereoselectivities observed in the epoxidation of al-Structural fine-tuning was probed through the angular delylic alcohols are of particular interest, as they give insight pendence of the diastereoselectivity for the conforinto the transition-state geometry. [4] mationally fixed cis-and trans-5-tert-butyl-2-cyclohexenols. The transition states of epoxidations are affected by both the steric and the electronic influences of substituents, and these determine the sense and the extent of the diastereose-Results and Discussion lectivity.…”
Section: Introductionmentioning
confidence: 99%
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“…A review covering the use of these tools would demand the citation of more than two thousand references. Without going to this extreme, one may select references that show the use of these mechanistic tools in organic, [6][7][8] organometallic, [9][10][11] and inorganic chemistry, [12][13][14][15][16][17] in electrochemistry, [18][19][20][21][22][23] in photochemistry [24][25][26] and in enzymatic catalysis. [27][28][29][30][31] In this work we deal with radical probes based on intramolecular additions of aryl radicals to unsaturated systems suitably positioned in substituents situated in ortho positions to the aryl radicals.…”
Section: Introductionmentioning
confidence: 99%
“…[6] However, in view of the carcinogenicity of chromium compounds, environmental and health concerns greatly limit their use. Although the dehydrogenating properties of PhIO and PhI(OAc) 2 have been demonstrated in a few cases, only a limited number of clean and selective catalytic oxidations of alcohols to carbonyl compounds have been reported.…”
mentioning
confidence: 99%