BiOClO 4 -mediated deprotection of silyl ethers

Crouch, R. David; Romany, Candice A.; Kreshock, Anna C.; Menconi, Karina A.; Zile, Jennifer L.

doi:10.1016/j.tetlet.2003.11.134

Cited by 26 publications

(2 citation statements)

References 21 publications

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“…Crouch and co-workers have reported that BiOClO 4 (1 equivalent) in CH 2 Cl 2 is an efficient reagent for the selective cleavage of alkyl silyl ethers (Scheme 42). 83 While moderate selectivity could be obtained in the cleavage of a bis-silyl protected compound, with selective cleavage of the TBDMS group over a TBDPS group, prolonged reaction times led to deprotection of both groups. While the authors do not report any problems in handling BiOClO 4 , the use of elevated reaction temperatures and stoichiometric amounts of BiOClO 4 call for considerable caution especially if this method is applied on a large scale.…”

Section: Bismuth(iii) Salts Catalyzed Deprotection and Formation Of S...mentioning

confidence: 99%

Applications of bismuth(iii) compounds in organic synthesis

2011

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8388 5.3. Formation of acetals catalyzed by bismuth(III) triflate 8388 5.4. Formation of 1,l-diacetates (acylals) 8389 5.5. Cleavage of epoxides catalyzed by bismuth(III) chloride 8389 5.6. Glycosylation promoted by bismuth(III) chloride 8389 5.7. Selective hydrolysis of aryl esters using bismuth(III) mandelate 5.8. Carbon-sulfur bond formation 5.8.1. Synthesis of thioacetals 8389 5.8.2. Conversion of epoxides to thiiranes 8390 5.9. Sulfonylation of aromatics 8390 5.10. Synthesis of sulfides and selenides promoted by Sm-BiCI3 8391 5.11. Synthesis of allyl sulfides 8391 5. 12. Formation of carbon-halogen bonds 8391 5.12.1. Synthesis of �-haloketones and esters 8391 5.12.2. Chlorination of alcohols catalyzed by bismuth(III) salts 8391 5.12.3. Synthesis of peracetylated glycosyl halides 8392 6. Reductions with bismuth compounds 8392 6.1. Selective reduction of nitro compounds to azoxy compounds 8392 6.2. Reduction of nitro compounds to amines 8392 6.3. Chemoselective reduction of a,�-unsaturated ethyl esters using BiCI3-NaBH 4 8392 6.4. Reduction of aromatic a-haloketones 8393 6.5. Miscellaneous reductions 8393 7. Rearrangements promoted by bismuth(III) salts 8393 7.1. Rearrangement of epoxides 8393 7.2. Allylic rearrangement of glycols (the Ferrier rearrangement) 8394 8. Conclusions

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Section: Bismuth(iii) Salts Catalyzed Deprotection and Formation Of S...mentioning

confidence: 99%

Applications of bismuth(iii) compounds in organic synthesis

2011

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“…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.…”

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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

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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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Protection for the Hydroxyl Group, Including 1,2‐ and 1,3‐Diols

2014

Greene's Protective Groups in Organic Synthesis

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BiOClO 4 -mediated deprotection of silyl ethers

Cited by 26 publications

References 21 publications

Applications of bismuth(iii) compounds in organic synthesis

Applications of bismuth(iii) compounds in organic synthesis

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

Protection for the Hydroxyl Group, Including 1,2‐ and 1,3‐Diols

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