Dysprosium(III) trifluoromethanesulfonate is a water-tolerant Lewis acid used in the Aldol reaction of silyl enol ethers with aldehydes. This is an effective catalyst for electrophilic substitution reactions of indoles with imines. Also used as catalyst for Aza-Piancatelli rearrangement, Friedel-Crafts alkylation, ring-opening polymerization reactions, microwave-assisted Kabachnik-Fields condensation, cycloaddition reactions (Lewis-acid catalyst), fries rearrangement and enantioselective glyoxalate-ene reactions.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Dysprosium(III) trifluoromethanesulfonate is a water-tolerant Lewis acid used in the Aldol reaction of silyl enol ethers with aldehydes. This is an effective catalyst for electrophilic substitution reactions of indoles with imines. Also used as catalyst for Aza-Piancatelli rearrangement, Friedel-Crafts alkylation, ring-opening polymerization reactions, microwave-assisted Kabachnik-Fields condensation, cycloaddition reactions (Lewis-acid catalyst), fries rearrangement and enantioselective glyoxalate-ene reactions.
Solubility
Soluble in water.
Notes
Hygroscopic. store away from water/moisture. Store in cool. Keep container tightly closed in a dry and well-ventilated place. Store away from oxidizing agent.
RUO – Research Use Only
General References:
- Leoni I Palmer; Javier Read de Alaniz. Direct and highly diastereoselective synthesis of azaspirocycles by a dysprosium(III) triflate catalyzed aza-Piancatelli rearrangement. Angewandte Chemie. International edition in English. 2011, 50 (31), 7167-7170.
- Patrick D Pohlhaus; Shanina D Sanders; Andrew T Parsons; Wei Li, Jeffrey S Johnson. Scope and mechanism for lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: evidence for a stereospecific intimate ion pair pathway. Journal of the American Chemical Society. 2008, 130 (27), 8642-8650.
- The uses of rare-earth metal triflates in organic synthesis have been reviewed by S. Kobayashi: Synlett, 689 (1994); Chem. Rev., 102, 2227 (2002).