Metal Triflates METALS • INORGANICS • ORGANOMETALLICS • CATALYSTS • LIGANDS • NANOMATERIALS • CUSTOM SYNTHESIS • CGMP FACILITIES • Aluminum • Europium • Lutetium • Silicon • Barium • Fluorine • Magnesium • Silver • Bismuth • Gadolinium • Molybdenum • Terbium • Calcium • Gallium • Neodymium • Thallium • Cerium • Holmium • Nickel • Thulium • Cobalt • Indium • Praseodymium • Tin • Copper • Iron • Rhodium • Ytterbium • Dysprosium • Lanthanum • Ruthenium • Yttrium • Erbium • Lead • Samarium • Zinc • Lithium • Scandium 13-150013-1500 Aluminum trifluoromethanesulfonate, 99% (Aluminum triflate) (74974‑61‑1) 10g Al(CF3SO3)3; FW: 474.18; white pwdr.; m.p. dec. 50g hygroscopic 56-810056-8100 Barium trifluoromethanesulfonate, 99% (Barium triflate) (2794‑60‑7) 5g HAZ Ba(CF3SO3)2; FW: 435.47; white pwdr.; m.p. dec. 25g hygroscopic 83-800083-8000 Bismuth(III) trifluoromethanesulfonate, min. 98% (Bismuth triflate) (88189‑03‑1) 1g Bi(SO3CF3)3; FW: 656.19; white to off-white pwdr. 5g hygroscopic 25g Technical Note: 1. Powerful Lewis acid useful in a number of catalytic reactions. References: 1. Synlett, 2003, 10, 1566 20-500020-5000 Calcium trifluoromethanesulfonate, min. 96% (Calcium triflate) (55120‑75‑7) 10g Ca(CF3SO3)2; FW: 338.21; white pwdr.; m.p. dec. 50g hygroscopic 58-600058-6000 Cerium(III) trifluoromethanesulfonate, min. 98% (Cerium triflate) (76089‑77‑5) 5g Ce(CF3SO3)3; FW: 587.33; white pwdr. 25g hygroscopic 27-049527-0495 Cyclic-Oligo Bis[(1R,2R)-(+)-1,2-cyclohexanediamino-N,N’-bis(3,3’-di-t-butylsalicylidene) cobalt(III)triflate]-5,5’-bis(2- 100mg carboxyethyl)ether (647036‑07‑5) 500mg C70H84Co2F6N4O20S2; FW: 1597.42; black xtl. Technical Notes: 1. Oligomeric catalyst used for the hydrolytic kinetic resolution of terminal epoxides under solvent-free conditions. 2. Oligomeric catalyst used for the synthesis of highly enantioenriched trans-1,2-amino alcohols. OH O O O Co catalyst O O +H2O + OH Tech. Note (1) C C C Ref. (1) H CO H3CO H3CO 3 >99% ee O O C H O O N (salen)Co-OTf + C (-PhOH) H2N OPh Tech. Note (2) Ref. (2) HO NH2 References: 1. Tetrahedron: Asymmetry, 2003, 14, 3633 2. Org. Lett., 2013, 15, 2895 3. Tetrahedron 2014, 70, 4165 27-049627-0496 Cyclic-Oligo Bis[(1S,2S)-(-)-1,2-cyclohexanediamino-N,N’-bis(3,3’-di-t-butylsalicylidene) cobalt(III)triflate]-5,5’-bis(2- 100mg carboxyethyl)ether (1252661‑94‑1) 500mg C70H84Co2F6N4O20S2; FW: 1597.42; black xtl. Technical Notes: 1. Oligomeric catalyst used for the hydrolytic kinetic resolution of terminal epoxides under solvent-free conditions. 2. Catalyst used for the synthesis of enantioenriched tetrahydrofurans via the intramolecular openings of oxetanes. 3. Catalyst for the enantioselective addition of phenyl carbamate to meso-epoxides for the synthesis of trans-1,2-amino alcohols. Visit www.strem.com for new product information and a searchable catalog. Strem Chemicals, Inc. Strem Chemicals, Inc. Strem Chemicals, Inc. Strem Chemicals UK Ltd. An Independent Distributor of Strem Chemicals Products 7 Mulliken Way 15, rue de l’Atome Postfach 1215 Newton Hall, Town Street Newburyport, MA 01950 Zone Industrielle 77672 KEHL Newton, Cambridge U.S.A 67800 BISCHHEIM France Germany England CB22 7ZE Tel: 978.499.1600 Tel: (33) 03 88 62 52 60 Tel: 0 78 51/ 7 58 79 Tel: 0845 643 7263 Fax: 978.465.3104 Fax: (33) 03 88 62 26 81 Fax:0845 643 7362 Email: [email protected] Email: [email protected] Email: [email protected] Email: [email protected] 1 0617 Metal Triflates O O OH O Co catalyst O + MeO O Tech. Note (1) MeO MeO H Ref. (1) O O O R Co catalyst R Tech. Note (2) OH Ref. (2) OH O O O O NH HO NH3Cl Tech. Note (3) Co catalyst KOH then HCl Ref. (3) + H2N OPh References: 1. Tetrahedron: Asymmetry, 2003, 14, 3633. 2. J. Am. Chem. Soc. 2009, 131, 2786. 3. Org. Lett., 2013, 15, 2895. COPPER (Compounds) 29-500029-5000 Copper(II) trifluoromethanesulfonate, 98% (Copper triflate) (34946‑82‑2) F F 5g F O O F HAZ Cu(CF3SO3)2; FW: 361.68; light green solid 25g hygroscopic S Cu2+ S 100g F O- -O F O O Technical Notes: 1. Ring-Opening of epoxides and aziridines. 2. Asymmetric conjugate addition of organozinc reagents to α,β-unsaturated ketones. 3. Electrophilic addition of olefins. 4. Asymmetric aziridination of olefins. 5. Asymmetric cycloadditions and aldol condensations. 6. Asymmetric Kharasch oxidation. 7. Asymmetric Michael addition of enamides. 8. Asymmetric O-H or O-R insertion reactions. 9. Enantioselective intramolecular aminooxygenation of alkenes. 10. Enantioselective addition of dialkylzinc reagents to N-acylpyridinium salts. 11. Pd-catalyzed C-H functionalizations of oximes with arylboronic acids. 12. Used as a Lewis acid in the Nazarov cyclization. 13. Catalyst in the diacetoxylation olefins 14. Catalyst in the meta-selective direct arylation of α-aryl carbonyl compounds 15. Catalyst in the three-component coupling of amines, aldehydes, and alkynes YH Cu(OTf)2 Y + PhNH2 Tech. Note (1) NHPh Ref. (1,2) Y= O, NPh O O Cu(OTf)2 / L* + Et Zn Tech. Note (2) 2 Ref. (4) Et 2 2 R R Cu(OTf)2 / L* NTs + PhI NTs R1 Tech. Note (4) R3 * R1 * Ref. (6) R3 O O Cu(OTf)2 / L* + OEt OEt Tech. Note (5) H Ref. (8) O O PhCO Cu(OTf)2 / L* 2 Tech. Note (6) ( )n + PhCO3-t-Bu * ( )n Ref. (7) PhNHNH2 Visit www.strem.com for new product information and a searchable catalog. Strem Chemicals, Inc. Strem Chemicals, Inc. Strem Chemicals, Inc. Strem Chemicals UK Ltd. An Independent Distributor of Strem Chemicals Products 7 Mulliken Way 15, rue de l’Atome Postfach 1215 Newton Hall, Town Street Newburyport, MA 01950 Zone Industrielle 77672 KEHL Newton, Cambridge U.S.A 67800 BISCHHEIM France Germany England CB22 7ZE Tel: 978.499.1600 Tel: (33) 03 88 62 52 60 Tel: 0 78 51/ 7 58 79 Tel: 0845 643 7263 Fax: 978.465.3104 Fax: (33) 03 88 62 26 81 Fax:0845 643 7362 Email: [email protected] Email: [email protected] Email: [email protected] Email: [email protected] 0617 2 Metal Triflates O OTMS R2 OH O 1 Cu(OTf)2 / L* 1 2 OR + R O Tech. Note (7) R S-t-Bu * S-t-Bu Ref. (11) O R3 O O O O O NHAc + Cu(OTf)2 / L* ArO OAr ArO OAr Tech. Note (8) 2 R then HBr R' Ref. (12) R' R2 O O O Cu(OTf)2 / L* Ar Ar + ROH Tech. Note (9) OMe RO OMe Ref. (13) H2O N2 H NHR R Cu(OTf) 2 N O N Tech. Note (10) Ref. (14) TEMPO O OMe 1. ClCO2Bn Tech. Note (11) Ref. (15) 2. Cu(OTf) / L N R N 2 R2Zn CO2Bn OMe OMe Pd(OAc) R N 2 R N Cu(OTf) 2 Tech. Note (12) H Ar Ref. (16) ArB(OH)2 R' R' O O O O O O Cu(OTf) OMe 2 Tech. Note (13) Ref. (17) OMe Ar Ar Cu(OTf) 2 OAc (10 mol %) R2 R2 R1 R1 Tech. Note (14) PhI(OAc)2 OAc Ref. (18) CH2Cl2, AcOH 40 °C X X Cu(OTf)2 R2 (5 mol %) R2 O O Tech. Note (15) Ar2IOTf Ref. (19) R1 DCE, 70 °C R1 Ar Cu(OTf)2 R3 R4 O (10 mol %) N R3 R4 R1 ++N H R2 R2 H toluene R1 References: 1. J. Org. Chem., 1999, 64, 287 11. Angew. Chem. Int. Ed., 2007, 46, 7803 2. J. Org. Chem., 1999, 64, 2537 12. J. Am. Chem. Soc., 2006, 128, 4594 3. J. Org. Chem., 1998, 63, 4568 13. J. Am. Chem. Soc., 2008, 130, 17638 4. (a) Eur. J. Org. Chem., 2002, 3221, b, J, Am, Chem, Soc, 2006, 128, 8416 14. Angew. Chem. Int. Ed., 2009, 48, 9339 5. Heterocycles, 1997, 45, 847 15. Org. Lett., 2010, 12, 184 6. J. Am. Chem. Soc., 1993, 115, 5328 16. J. Am. Chem. Soc., 2008, 130, 1003 7. Acc. Chem. Res., 2000, 33, 325 17. Org. Lett., 2010, 12, 1412 8. J. Am. Chem. Soc., 2001, 123, 3830 18. Angew. Chem. Int. Ed., 2011, 50, 463 9. Angew. Chem. Int. Ed., 2001, 40, 3567 19. Org. Lett., 2012, 14, 964 10. Tetrahedron, 2002, 58, 845 Visit www.strem.com for new product information and a searchable catalog. Strem Chemicals, Inc. Strem Chemicals, Inc. Strem Chemicals, Inc. Strem Chemicals UK Ltd. An Independent Distributor of Strem Chemicals Products 7 Mulliken Way 15, rue de l’Atome Postfach 1215 Newton Hall, Town Street Newburyport, MA 01950 Zone Industrielle 77672 KEHL Newton, Cambridge U.S.A 67800 BISCHHEIM France Germany England CB22 7ZE Tel: 978.499.1600 Tel: (33) 03 88 62 52 60 Tel: 0 78 51/ 7 58 79 Tel: 0845 643 7263 Fax: 978.465.3104 Fax: (33) 03 88 62 26 81 Fax:0845 643 7362 Email: [email protected] Email: [email protected] Email: [email protected] Email: [email protected] 3 0617 Metal Triflates 29-500129-5001 Copper(II) trifluoromethanesulfonate, 99% (99.9%-Cu) (Copper triflate) (34946‑82‑2) F F 5g F O O F HAZ Cu(CF3SO3)2; FW: 361.68; light green solid 25g air sensitive S Cu2+ S 100g F O- -O F O O 66-400066-4000 Dysprosium(III) trifluoromethanesulfonate, min. 98% (Dysprosium triflate) (139177‑62‑1) 5g Dy(CF3SO3)3; FW: 609.71; white solid 25g hygroscopic 68-600068-6000 Erbium(III) trifluoromethanesulfonate, min. 98% (Erbium triflate) (139177‑64‑3) 5g Er(CF3SO3)3; FW: 614.47; pink pwdr. 25g hygroscopic 63-100063-1000 Europium(III) trifluoromethanesulfonate, min. 98% (Europium triflate) (52093‑25‑1) 1g Eu(CF3SO3)3; FW: 599.17; white to off-white pwdr.