Effective oxidation of benzylic and aliphatic alcohols with hydrogen peroxide catalyzed by a manganese(III) Schiff-base complex under solvent-free conditions

Mardani, Hamid Reza; Golchoubian, Hamid

doi:10.1016/j.tetlet.2006.02.007

Cited by 55 publications

(24 citation statements)

References 32 publications

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“…As indicated in Scheme 4, oxidation of 3-phenyl-1-propanol did not occur, while oxidation of alcohols with this system and in the absence of Me 3 SiCl and H 2 O was reported to occur efficiently [24]. So we assume that Me 3 SiOH a Yields refer to isolated products; the products were identified by comparison of physical and spectroscopic properties with authentic compounds.…”

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confidence: 90%

“…Recently, our research group reported H 2 O 2 -oxidation of hydrocarbons [23], alcohols [24], sulfides [25] and coupling of thiols [26] using Mn(III) Schiff-base complex as a catalyst. Having these data in hand and in continuation of our research in improvement of deprotection systems [27], we decided to join together catalysis feature of outlined transition metal complex with safe oxidative ability of H 2 O 2 in the deprotection of silyl and THP ethers as major protective groups for hydroxyl compounds.…”

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confidence: 99%

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Chemoselective and Efficient Method for Deprotection of THP and Silyl Ethers with H2O2/ Mn(III) Schiff-Base Complex

Tajbakhsh¹,

Hosseinzadeh²,

Golchoubian³

et al. 2008

LOC

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Mn(III) Schiff-base complex as a catalyst with H 2 O 2 was applied for oxidative deprotection of THP ethers to the corresponding carbonyl compounds and conversion of silyl ethers into the parent alcohols under mild conditions. Chemoselective cleavage of trimethylsilyl ethers in the presence of t-butyldimethylsilyl ethers and cleavage of trimethylsilyl ethers in the presence of tetrahydropyranyl ethers were also achieved with this system. Keywords: THP ether, silyl ether, deprotection, Mn(III) Schiff-base complex, hydrogen peroxide.Ether deprotection methodologies play an important role in organic, medicinal and carbohydrate chemistry as well as the chemistry of drug design [1]. In spite of existing several deprotection systems [2][3][4][5][6][7][8][9][10][11], new selective and eco-efficient methods are still required. In terms of economical and environmental concern, catalytic processes with inexpensive and environmental friendly reagents are extremely valuable. One of favorite reagents to resort is hydrogen peroxide due to its several advantages; H 2 O 2 is the ultimate green reagent because water is the only by-product [12], it furnishes 47% of its weight as oxidant, which is much more than other common oxidant such as NaClO, KHSO 5 and ROOH. Aqueous H 2 O 2 is a stable reagent only if H 2 O 2 -decomposition catalysts, like Fe salts, are rigorously excluded [13]. Although a variety of different catalytic systems for the hydrogen peroxide oxidation have been developed [14], there is a growing interest in the search for new efficient metal catalysts for this concern [15]. One of the exciting results of catalytic research is development of transition metal catalyst that employs H 2 O 2 to selective oxidation of organic compounds such as alcohols, hydrocarbons and sulfides [16][17][18].Recently, use of metal Schiff-base complexes, i.e. metal salen and metal solaphen to catalyze the oxidation process have received much attention, for example, oxidation of primary aromatic amines, aerobic oxidation of alcohols and hydrocarbons as well as oxidative decarboxylation of carboxylic acids [19][20][21][22]. Recently, our research group reported H 2 O 2 -oxidation of hydrocarbons [23], alcohols [24], sulfides [25] and coupling of thiols [26] using Mn(III) Schiff-base complex as a catalyst. Having these data in hand and in continuation of our research in improvement of deprotection systems [27], we decided to join together catalysis feature of outlined transition metal complex with safe oxidative ability of H 2 O 2 in the deprotection of silyl and THP ethers as major protective groups for hydroxyl compounds.Mn(III) Schiff-base complex was easily prepared by a procedure similar to that used by Karmaker, using 1,2-diaminoethane instead of 1,3-diaminopropane [28]. The starting materials are cheap and available in every laboratory. It is homogeneous solid, non-hygroscopic which can be stored for months without losing its activity and so safe to handle. Complex (1). O N N Mn Clo 4 -O + Complex 1.Herein, we wish to report our meth...

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confidence: 90%

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confidence: 99%

Chemoselective and Efficient Method for Deprotection of THP and Silyl Ethers with H2O2/ Mn(III) Schiff-Base Complex

Tajbakhsh¹,

Hosseinzadeh²,

Golchoubian³

et al. 2008

LOC

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“…In the past decade, tremendous efforts have been devoted to homogeneous catalysts for benzylic oxidation [13][14]. For example, transition metal salts and complexes containing Cr(CO) 6 [15], CoCl 2 [16], Co(OAc) 2 ·4H 2 O [17], Mn(salen) [18][19], RuCl 3 [20][21], RuCl 2 (PPh 3 ) 3 [22], Rh 2 (cap) 4 [23] or Cp 2 VCl 2 [24] have been shown to be good homogeneous catalysts for benzylic oxidation. However, the development of catalysts that are clean, inexpensive, efficient and selective and which reach the standards of green chemistry remains a challenging goal.…”

Section: Introductionmentioning

confidence: 99%

Monodispersed poly(4-vinylpyridine) spheres supported Fe(III) material: An efficient and reusable catalyst for benzylic oxidation

Fan

Luan

Wang

et al. 2015

Journal of Molecular Catalysis A: Chemical

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“…In continuation of our current studies in the selective oxidation of hydrocarbons [21,22] we wish to report a very efficient and simple method for oxidative coupling of alkyl or aryl thiols into the corresponding disulfides using urea-hydrogen peroxide (UHP) catalyzed by the Mn(III) Schiff-base complex 1 under mild conditions as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Mild and highly efficient transformation of thiols to symmetrical disulfides using urea–hydrogen peroxide catalyzed by a Mn(III)–salen complex

Hosseinpoor

Golchoubian

2006

Catal Lett

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Effective oxidation of benzylic and aliphatic alcohols with hydrogen peroxide catalyzed by a manganese(III) Schiff-base complex under solvent-free conditions

Cited by 55 publications

References 32 publications

Chemoselective and Efficient Method for Deprotection of THP and Silyl Ethers with H2O2/ Mn(III) Schiff-Base Complex

Chemoselective and Efficient Method for Deprotection of THP and Silyl Ethers with H2O2/ Mn(III) Schiff-Base Complex

Monodispersed poly(4-vinylpyridine) spheres supported Fe(III) material: An efficient and reusable catalyst for benzylic oxidation

Mild and highly efficient transformation of thiols to symmetrical disulfides using urea–hydrogen peroxide catalyzed by a Mn(III)–salen complex

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