2011
DOI: 10.1039/c0cs00206b
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Applications of bismuth(iii) compounds in organic synthesis

Abstract: 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 prom… Show more

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Cited by 237 publications
(104 citation statements)
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References 362 publications
(303 reference statements)
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“…Recently, the interest in poor metals and metalloids in energy storage devices is growing up. Among them, bismuth seems to be a good candidate because of nontoxic character in comparison to the neighbors from the periodic table, namely, lead and antimony [3]. Generally, bismuth chemistry is mainly focused on medical and catalytic applications.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Recently, the interest in poor metals and metalloids in energy storage devices is growing up. Among them, bismuth seems to be a good candidate because of nontoxic character in comparison to the neighbors from the periodic table, namely, lead and antimony [3]. Generally, bismuth chemistry is mainly focused on medical and catalytic applications.…”
Section: Introductionmentioning
confidence: 99%
“…Generally, bismuth chemistry is mainly focused on medical and catalytic applications. In medicine, bismuth compounds are most commonly used for treating gastrointestinal disorders [4] while in organic synthesis may be applied in Friedel-Crafts acylation, Michael reactions, synthesis of lactones, and oxidation of thiols [3]. Bismuth is a relatively inexpensive material, in comparison to most extensively studied ruthenium [5], and can be obtained as a byproduct in copper, lead, and tin mining.…”
Section: Introductionmentioning
confidence: 99%
“…We first used the acyclic b-ketoester 1 bearing a pendant trisubstituted allene as a model and assessed its reactivity towards various metal triflate catalysts in nitromethane (Table 1, entries 1-4). A rapid screening highlighted nonexpensive bismuth(III) triflate [9,10] as a very active catalyst at low loading with the total conversion of 1 occurring at À20 8C. Switching solvents from nitromethane to CH 2 Cl 2 considerably slowed down the reaction rate and led to the isolation of the cyclopentadienes 2 b and 2 c in good yield (88 %) at room temperature by using only 1 mol % of bismuth(III) triflate (entry 5).…”
mentioning
confidence: 98%
“…6,7,8,9 However, these compounds are susceptible to hydrolysis and react preferentially with water rather than the substrates.…”
Section: Introductionmentioning
confidence: 99%