A Rapid, Selective, and Efficient Method for Deprotection of Silyl Ethers Catalyzed by Bismuth(iii) Salts

Firouzabadi, Habib; Mohammadpoor‐Baltork, Iraj; Kolagar, S.

doi:10.1081/scc-100103326

Cited by 38 publications

(13 citation statements)

References 13 publications

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“…Unlike BiCl 3 or Bi(OCOCF 3 ) 3 , Bi(OTf) 3 also cleaves TBDMS ethers. [75] It was shown by competition experiments that TMS ethers can be deprotected selectively in the presence of TBDMS ethers. Scheme 41 …”

Section: Cleavage Of Silyl Ethersmentioning

confidence: 99%

Bismuth(III) Triflate in Organic Synthesis

2004

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Section: Cleavage Of Silyl Ethersmentioning

confidence: 99%

Bismuth(III) Triflate in Organic Synthesis

2004

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“…By this procedure, aliphatic TMS ethers were easily converted to the corresponding alcohols in good yields ( Table 2, entries 15 and 16). Similarly, phenolic and cyclic TMS ethers were converted to the corresponding hydroxyl compounds under this reaction condition (Table 2, entries 17,[21][22][23].…”

Section: Resultsmentioning

confidence: 99%

“…Deprotection of TMS ethers to their corresponding alcohols under mild reaction conditions is of practical importance and several methods and catalysts such as bismuth(III) salts, [23] NaBrO 3 -NH 4 Cl, [24] PhCH 2 PPh 3 HSO 5 , [25] Zr(KPO 4 ) 2 , [26] potassium dodecatungstocobaltate(III) trihydrate, [27] cobalt(II) tetrasulfophthalocyanine, [28] trimethylsilyl bromide, [29] CuBr 2 , [30] tetraethylammonium superoxide, [31] DABCO-bromine, [32] sulfated SnO 2 [33] and LiOAc [34] have been reported for this transformation. However, in some of the reported methods one or more disadvantages, such as harsh reaction conditions, high reaction temperatures, long reaction times, high cost or toxicity of the reagents have been experienced.…”

Section: Introductionmentioning

confidence: 99%

Rapid and efficient protection of alcohols and phenols, and deprotection of trimethylsilyl ethers catalyzed by a cerium‐containing polyoxometalate

Yadollahi

Mirkhani

Tangestaninejad

et al. 2010

Applied Organom Chemis

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Herein, we want to report a simple and convenient way for protection-deprotection of alcohols in the presence of ammonium decatungstocerate(IV) {(NH 4 ) 8 [CeW 10 O 36 ]·20H 2 O} as catalyst under ambient temperature in CH 3 CN. Using 0.002 mmol of the catalyst, various alcohols and phenols were transformed easily to the corresponding TMS ethers in excellent yields. In the second part, various TMS ethers were successfully converted to the parent hydroxyl compounds in the presence of the ammonium decatungstocerate(IV) catalyst.

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“…On the other hand, in recent years, economically affordable ecofriendly catalysts received some interest in various organic reactions. The application of some of these catalysts such as Cu(II) salts [14], Fe(II)/Fe(III) salts [15], nickel salts, and Bismuth(III) salts [16,17] as catalysts in organic synthesis, has been investigated extensively. Bismuth trichloride has received considerable attention as an inexpensive, nontoxic, and readily available catalyst for various organic transformations, affording the corresponding products in excellent yields with high selectivity (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%