Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents

Moorthy, Jarugu Narasimha; Singhal, Nidhi; Senapati, Kalyan

doi:10.1016/j.tetlet.2007.11.013

Cited by 67 publications

(45 citation statements)

References 36 publications

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“…Nevertheless, they will play an important role in designing new mechanistic experiments. For example, computational work by Goddard 53,54 and Legault 55 has shown that some iodine(V) and iodine(III) compounds must undergo a “hypervalent twist” before a bound substrate can undergo oxidation. This twisting was also incorporated into Quideau’s proposed mechanisms for ortho- hydroxylation.…”

Section: Known Unknownsmentioning

confidence: 99%

Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Harned

2014

Tetrahedron Letters

101

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The use of and λ3- and λ5-iodanes in the oxidative dearomatization of phenols is a well-established and general procedure for the construction of cyclohexadienone structures. However, their use in asymmetric dearomatization reactions is quite underdeveloped and, despite work by several research groups over the past several years, a general chiral aryl iodide catalyst has yet to emerge. This article will serve to highlight the significant progress that has been made in this area and will reveal some of deficiencies in the literature that the author believes may be hindering further progress.

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Section: Known Unknownsmentioning

confidence: 99%

Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Harned

2014

Tetrahedron Letters

101

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“…The obtained results indicate that catalyst is not prone to decomposition and the polymeric nature of catalyst is preserved throughout sulfide oxidation. 2 ] n as the catalyst in the presence of oxone and tetra-n-butylammonium bromide as phase transfer agent (entries 1-5). When the reaction was carried out in CH 2 Cl 2 , the conversion of benzyl alcohol was higher than in CH 3 Cl, CH 3 CN, CH 3 COCH 3 or n-hexane.…”

Section: Sulfide Oxidationmentioning

confidence: 99%

Synthesis, X‐ray structure, characterization and catalytic activity of a polymeric manganese(II) complex with iminodiacetate

Bagherzadeh

Amini

Boghaei

et al. 2011

Applied Organom Chemis

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A polymeric manganese(II) complex with the general formula [Mn(O 2 CCH 2 NH 2 CH 2 CO 2 ) 2 (H 2 O) 2 ] n from reaction of iminodiacetatic acid and manganese(II) perchlorate under nitrogen in water, was synthesized and characterized. The structure of the complex was determined using single-crystal X-ray diffraction, elemental analysis, IR and UV-vis spectra. This complex exhibited excellent catalytic activity and selectivity for oxidation of various alcohols and sulfides to the corresponding aldehydes/ketone and sulfoxides using urea hydrogen peroxide and oxone (2KHSO 5 ·KHSO 4 ·K 2 SO 4 ), respectively, as oxidants under air at room temperature. The easy preparation, mild reaction conditions, high yields of the products, short reaction time, no over-oxidation products, high selectivity and inexpensive system make this catalytic system a useful method for oxidizing various alcohols and sulfides.

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“…So löst sich das methylsubstituierte IBX-Derivat 6 auch zu geringen Teilen in Aceton, Acetonitril, Ethylacetat und Tetrahydrofuran, sodass in diesen Lösungsmitteln bei Raumtemperatur sowohl eine Oxidation von Alkoholen zu den ent-sprechenden Carbonylverbindungen als auch von Sulfiden zu den entsprechenden Sulfoxiden möglich war. [32] Vinod und Mitarbeiter zeigten, dass durch Einführung einer zusätzlichen Carbonsäuregruppe wasserlösliche IBX-Derivate wie mIBX (7) und 8 erhalten werden. Benzylische und allylische Alkohole konnten durch mIBX in Wasser oder wässrigem THF effektiv oxidiert werden.…”

Section: Herstellung Von Ibxunclassified

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

Duschek

Kirsch

2011

Angewandte Chemie

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Seit seiner Entdeckung durch Christoph Hartmann und Victor Meyer im Jahr 1893 hat sich 2‐Iodoxybenzoesäure (IBX) zu einem geradezu ubiquitär einsetzbaren Oxidationsmittel entwickelt. Insbesondere in den vergangenen zehn Jahren wurde eine Vielzahl von Anwendungsmöglichkeiten beschrieben, die weit über die einfache Oxidation von Alkoholen hinausgehen. Dieser Aufsatz behandelt das Potenzial von IBX in der Synthese, wobei insbesondere unerwartete Reaktivitäten und moderne Anwendungen im Mittelpunkt der Diskussion stehen.

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Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents

Cited by 67 publications

References 36 publications

Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Synthesis, X‐ray structure, characterization and catalytic activity of a polymeric manganese(II) complex with iminodiacetate

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

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