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 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

Mortar-Pestle and Microwave Assisted Regioselective Nitration of Aromatic Compounds in Presence of Certain Group V and VI Metal Salts under Solvent Free Conditions

“…The above mentioned disadvantages of the commercial manufacturing process currently used have led to a substantial effort to develop viable alternatives. Quite often either metal nitrates or metal nitrates supported on silica, alumina or clay [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] have been used as catalysts in the alternate methods of nitration to overcome the problems of classical nitration. In recent past Bismuth (III) compounds have received particular attention as low toxicity reagents and catalysts for various organic transformations [11,12].…”

Avaliação da natureza da atividade catalítica de compostos de bismuto em reações de metanólise do óleo de soja

“…Além disso, compostos de bismuto exibem acidez de Lewis de moderada a forte devido à blindagem deficiente do núcleo pelos elétrons f do átomo de bismuto (Bi = [Xe] 4f 14 , 5d 10 , 6s 2 , 6p 3 ). [18][19][20][21][22][23][24] Por consequência, o comportamento catalítico destes compostos tem sido investigado em diferentes tipos de reações químicas, exceto em reações de transesterificação, onde sua aplicação catalítica ainda é desconhecida. Por outro lado, o sólido NaBiO 3 ·2H 2 O também é frequentemente utilizado na determinação de manganês em ferro e aço.…”

The First Synthesis of p-Cl- and p-F-Phenylverbenene

“…Although their chemistry is not well known, bismuth salts have been widely used as Lewis acids to catalyze numerous reactions, mainly functional group deprotections, oxidations, reductions, rearrangements and C-C bond formation [1]. The last of these reactions can be achieved by Friedel-Crafts acylation, aldolic and Knoevenagel condensations, Diels-Alder cycloaddition, and Michael addition, to mention just a few possibilities [2]. Recently, bismuth has also been used in the chemistry of natural products [3].…”