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Bismuth(III) trifluoromethanesulfonate acts as a catalyst in Friedel-Crafts acylation and cycloisomerization of allene-enol ethers. It behaves as a direct substitution catalyst and involved in the substitution of allylic, propargylic, and benzylic alcohols with sulfonamides, carboxamides and carbamates. Further, it is also used in Mukaiyama aldol reactions.
Mild Lewis acid catalyst for high-yield acylation of alcohols: Angew. Chem. Int. Ed., 39, 2877 (2000), and Friedel-Crafts acylation of aromatics, effective at 5-10 mol%: Tetrahedron Lett., 38, 8871 (1997); Eur. J. Org. Chem., 2743 (1998). For use in the Claisen rearrangement of allyl ethers and the Fries rearrangement of phenyl esters, see: Synth. Commun., 34, 1433 (2004); Synlett, 2794 (2004); Tetrahedron Lett., 47, 4051 (2006). Aromatic sulfonylation can also be effected with sulfonyl chlorides: J. Org. Chem., 64, 6479 (1999). At 0.1-0.5 mol%, catalyzes the acylation of primary and secondary alcohols with anhydrides in high yield under mild conditions: J. Org. Chem., 66, 8926 (2001); see also Synthesis, 2091 (2001). For a review of acylation and sulfonylation reactions, see: Synlett, 181 (2002).
Promotes the rearrangement of aryl-substituted epoxides to aldehydes and ketones: Tetrahedron Lett., 42, 8129 (2001). Catalyzes the deprotection of acetals and ketals under mild conditions: J. Org. Chem., 67, 127 (2002), and also the rapid cleavage of thioacetals: Tetrahedron Lett., 44, 2857 (2003). Catalyzes the allylation of aldehydes with Allyltri-n-butyltin, L14087, to give homoallylic alcohols: Synlett, 1694 (2002); J. Org. Chem., 70, 2091 (2005), and of acetals with Allyltrimethylsilane, A14662, providing a mild and efficient route to homoallyl ethers: Tetrahedron Lett., 43, 4597 (2002).
Catalyzes the Michael-type addition of a variety of primary and secondary aliphatic amines to ɑ,ß-unsaturated compounds (acrylates, etc.) to give the saturated amino derivatives: Synlett, 720 (2003).
The Ritter reaction of various nitriles with tert-alcohols to give tert-alkyl amides has been accomplished in high yield in the presence if a cataytic acmount of Bi(OTf)3: Tetrahedron Lett., 47, 8699 (2006).
It is also effective in inducing a direct catalytic three-component Mannich reaction of an aldehyde, an amine and a ketone in aqueous media to give a ß-amino ketone: Tetrahedron Lett., 47, 8457 (2006).
For a reviews on uses of this reagent in synthesis, see: Synlett, 1566 (2003); Eur. J. Org. Chem., 2517 (2004). For a review of applications of Bi(III) compounds in synthesis, see: Tetrahedron, 58, 8373 (2002).
Mohr, P.; Imhoff, M. P.; Reggiani, F. Stereoselective synthesis of pyrrolidines from beta'-amino-allylsilanes. Tetrahedron Lett. 2015, 56 (17), 2262-2264.
Fodili, M.; Nedjar-Kolli, B.; Vedrenne, M.; Saffon-Merceron, N.; Lherbet, C.; Hoffmann, P. The first example of an unusual rearrangement in the van Leusen imidazole synthesis. Chem. Heterocycl. Compd. 2015, 51 (10), 940-943.
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant