Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols

Ivan M. Geraskin; Matthew W. Luedtke; Heather M. Neu; Victor N. Nemykin; Viktor Zhdankin

doi:10.1016/j.tetlet.2008.10.060

Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols

Ivan M. Geraskin
, Matthew W. Luedtke
, Heather M. Neu
, Victor N. Nemykin
, Viktor Zhdankin

Research output: Contribution to journal › Article › peer-review

77 Scopus citations

Abstract

The pseudocyclic iodine(V) oxidants, such as esters of iodoxybenzoic acid (IBX-esters) and 2-iodylphenol ethers, can serve as stable and efficient sources of oxygen in catalytic oxidations, and their reactivity is similar to the commonly used thermally unstable and potentially explosive iodosylbenzene. In a specific example, primary or secondary benzylic alcohols are selectively oxidized by isopropyl IBX-ester in the presence of μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III) (0.1 mol equiv) in dichloromethane at room temperature in 0.5-2 h to afford the respective carbonyl compounds in 100% conversion and preparative yields 91-95% after column chromatography.

Original language	English (US)
Pages (from-to)	7410-7412
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.060
State	Published - Dec 22 2008

Bibliographical note

Funding Information:
This work was supported by a research Grant from the National Science Foundation (Grant CHE-0702734) and Petroleum Research Fund, administered by the American Chemical Society (Grant PRF-45510-GB-3).

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@article{46fb43f62c134eb6ad48f2f1fc64a3f7,

title = "Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols",

abstract = "The pseudocyclic iodine(V) oxidants, such as esters of iodoxybenzoic acid (IBX-esters) and 2-iodylphenol ethers, can serve as stable and efficient sources of oxygen in catalytic oxidations, and their reactivity is similar to the commonly used thermally unstable and potentially explosive iodosylbenzene. In a specific example, primary or secondary benzylic alcohols are selectively oxidized by isopropyl IBX-ester in the presence of μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III) (0.1 mol equiv) in dichloromethane at room temperature in 0.5-2 h to afford the respective carbonyl compounds in 100\% conversion and preparative yields 91-95\% after column chromatography.",

author = "Geraskin, \{Ivan M.\} and Luedtke, \{Matthew W.\} and Neu, \{Heather M.\} and Nemykin, \{Victor N.\} and Viktor Zhdankin",

note = "Funding Information: This work was supported by a research Grant from the National Science Foundation (Grant CHE-0702734) and Petroleum Research Fund, administered by the American Chemical Society (Grant PRF-45510-GB-3). ",

year = "2008",

month = dec,

day = "22",

doi = "10.1016/j.tetlet.2008.10.060",

language = "English (US)",

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pages = "7410--7412",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols

AU - Geraskin, Ivan M.

AU - Luedtke, Matthew W.

AU - Neu, Heather M.

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor

N1 - Funding Information: This work was supported by a research Grant from the National Science Foundation (Grant CHE-0702734) and Petroleum Research Fund, administered by the American Chemical Society (Grant PRF-45510-GB-3).

PY - 2008/12/22

Y1 - 2008/12/22

N2 - The pseudocyclic iodine(V) oxidants, such as esters of iodoxybenzoic acid (IBX-esters) and 2-iodylphenol ethers, can serve as stable and efficient sources of oxygen in catalytic oxidations, and their reactivity is similar to the commonly used thermally unstable and potentially explosive iodosylbenzene. In a specific example, primary or secondary benzylic alcohols are selectively oxidized by isopropyl IBX-ester in the presence of μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III) (0.1 mol equiv) in dichloromethane at room temperature in 0.5-2 h to afford the respective carbonyl compounds in 100% conversion and preparative yields 91-95% after column chromatography.

AB - The pseudocyclic iodine(V) oxidants, such as esters of iodoxybenzoic acid (IBX-esters) and 2-iodylphenol ethers, can serve as stable and efficient sources of oxygen in catalytic oxidations, and their reactivity is similar to the commonly used thermally unstable and potentially explosive iodosylbenzene. In a specific example, primary or secondary benzylic alcohols are selectively oxidized by isopropyl IBX-ester in the presence of μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III) (0.1 mol equiv) in dichloromethane at room temperature in 0.5-2 h to afford the respective carbonyl compounds in 100% conversion and preparative yields 91-95% after column chromatography.

UR - https://www.scopus.com/pages/publications/55549119207

UR - https://www.scopus.com/pages/publications/55549119207#tab=citedBy

U2 - 10.1016/j.tetlet.2008.10.060

DO - 10.1016/j.tetlet.2008.10.060

M3 - Article

AN - SCOPUS:55549119207

SN - 0040-4039

VL - 49

SP - 7410

EP - 7412

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols

Abstract

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