Selective Deprotection of tert-Butyldimethylsilyl Ethers Using Nafion-H®/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol

Synthetic Communications

Volumn 33, Issue 23, 2003, Pages 4043-4052

  Rani, Shikha ^a   Babu, J Lokesh ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Bromodimethyl sulphonium bromide; Nafion H NaI; Selective deprotection; TBDMS ethers

Indexed keywords

BENZYL DERIVATIVE; BROMODIMETHYLSULFONIUM BROMIDE; DIMETHYL ETHER; ETHER DERIVATIVE; METHANOL; PHENOL; SODIUM IODIDE; SULFONIUM DERIVATIVE; TERT BUTYLDIMETHYLSILYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DEPROTECTION REACTION;

EID: 0345598996     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120026345     Document Type: Article

References (51)

1. General Synthetic Methods, part 16. For part 15, see Kumareswaran, R.; Reddy, B.G.; Vankar, Y.D. Nafion-H-catalyzed mukaiyama aldol condensations and hetero diels-alder reactions using aldehydes and imines. Tetrahedron Lett. 2001, 42, 7493.
2. Corey, E.J.; Venkateswarulu, A. Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J. Am. Chem. Soc. 1972, 94, 6190.
3. (i) Greene, T.W.; Wuts, P.G. Protective Groups in Organic Synthesis, 3rd Ed.; John Wiley & Sons: New York, 1999;
4. (ii) Kocienski, P. Protecting Groups in Organic Synthesis; George Thieme Verlag: New York, 1994;
5. (iii) Bajwa, J.S.; J. Vivelo, J.; Slade, J.; Repic, O.; Blacklock, T. Selective deprotection of alkyl t-butyldimethylsilyl ethers in the presence of aryl t-butyldimethylsilyl ethers with bismuth bromide. Tetrahedron Lett. 2000, 41, 6021 and references cited therein;
6. (iv) Yang, Y.-Y.; Yang, W.-B.; Teo, C.-F.; Lin, C.-H. Regioselective deprotection of tert-butyldimethylsilyl ethers by boron trichloride. Synlett. 2000, 1634;
7. (v) Firouzabadi, H.; Mohammadpour-Baltork, I.; Kolagar, S. A rapid, selective and efficient method for deprotection of silyl ethers catalysed by bismuth (III) salt. Synth. Commun. 2001, 31, 905.
8. (a) Corey, E.J.; Jones, G.B. Reductive cleavage of tert-butyldimethylsilyl ethers by diisobutylaluminum hydride. J. Org. Chem. 1992, 57, 1028;
9. (b) de Vries, E.F.J.; Brussee, J.; van der Gen, A. Intramolecular reductive cleavage of tert-butyldimethylsilyl ethers. Selective mono-deprotection of bis-silyl-protected diols. J. Org. Chem. 1994, 59, 7133;
10. (c) Cormier, J.F. Removal of TBDMS protecting Groups from Carbohydrates using Catalytic Transfer Hydrogenation. Tetrahedron Lett. 1991, 32, 187.
11. (a) Datta Gupta, A.; Singh, R.; Singh, V.K. A Mild and Efficient Method for the Cleavage of tert Butyldimethylsilyl and Tetrahydropyranyl Ethers by Ceric Ammonium Nitrate in Methanol. Synlett. 1996, 69;
12. (b) Oku, A.; Kinugasa, M.; Kamada, T. Deprotection of Acetals and Silyl Ethers by DDQ. Is DDQ a Neutral Catalyst? Chem. Lett. 1993, 165;
13. (c) Tanemura, K.; Suzuki, T.; Horaguchi, T. J.C.S. Deprotection of Silyl Ethers using 2,3-Dichloro-5,6-Dicyano-p-Benzoquinone. Chem. Commun. 1992, 2997;
14. (d) Wang, M.J.; Li, C.; Yim, D.L.; Liang, X.-T. A Mild and Efficient Approach for the Deprotection of Silyl Ethers by Sodium Periodate. Tetrahedron Lett. 2002, 43, 8727;
15. (e) Sabitha, G.; Syamala, M.; Yadav, J.S. A Mild, Efficient, Inexpensive, and Selective-Cleavage, of Primany tert-Butyldimethylsilyl Ethers by Oxone in Aqueous Methanol. Org. Lett. 1999, 1, 1701.
16. (a) Zhang, W.; Robins, M.J. Removal of Silyl Protecting Groups from Hydroxyl Functions with Ammonium Fluoride in Methanol. Tetrahedron Lett. 1992, 33, 1177;
17. (b) Metcalf, B.W.; Burkhart, J.P.; Jund, K. Cleavage of tert-Butyldimethylsilyl Ethers by Tetrafluoroborate Salts. Tetrahedron Lett. 1980, 21, 35;
18. (c) Ranu, B.C.; Jana, U.; Majee, A. A Simple and Efficient Method for Selective Deprotection of t-Butldimethylsilyl Ethers by Zinc Tetrafluoroborate in Water. Tetrahedron Lett. 1999, 40, 1985;
19. (d) Corey, E.J.; Yi, K.Y. Tetrafluorosilane is a Mild and Very Selective Reagent for the Cleavage of Silyl-Protected Alcohols. Tetrahedron Lett. 1992, 33, 2289.
20. (a) Crouch, R.D.; Stieff, M.; Frie, J.L.; Cadwallader, A.B.; Bevis, D.C. Selective Deprotection of Silyl-Protected Phenols Using Solid NaOH and a Phase Transfer Catalyst. Tetrahedron Lett. 1999, 40, 3133;
21. (b) Wilson, N.S.; Keay, B.A. Mild Base Mediated Desilylation of Various Phenolic Silyl Ethers. Tetrahedron Lett. 1997, 38, 187.
22. (a) Hunter, R.; Hinz, W.; Richards, P. On the Chemoselectivity and Mechanism of Desilylation of tert-Butyldimethylsilyl Ethers with TMSOTf. Tetrahedron Lett. 1999, 40, 3643;
23. (b) Yang, Y.-Y.; Yang, W.-B.; Teo, C.-F.; Lin, C.-H. Regioselective Deprotection of tert-Butyldimethylsilyl Ethers by Boron Trichloride. Synlett. 2000, 1634;
24. (c) Grieco, P.A.; Markworth, C.J. Selective Deprotection of Alkyl t-Butyldimethylsilyl Ethers in the Presence of Aryl t-Butyldimethylsilyl Ethers. Tetrahedron Lett. 1999, 40, 665;
25. (d) Bartoli, G.; Cupone, G.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Procopio, A.; Sambri, L.; Tagarelli, A. Deprotection of t-Butyldimethylsilyl Ethers Promoted by Cerium(IV) Triflate. Tetrahedron Lett. 2002, 43, 5945;
26. (e) Kartha, K.P.R.; Field, R.A. Iodine and its Interhalogen Compounds: Versatile Reagents in Carbohydrate Chemistry IX. A Mild and Selective Deprotection of tert-Butyldimethylsilyl (TBDMS) Ethers in the Presence of Various Protecting Groups using Iodine Monobromide. Synlett. 1999, 311;
27. (f) Lipshutz, B.H.; Keith, J. Selective Deprotection of Alkyl vs. Aryl Silyl Ethers. Tetrahedron Lett. 1998, 39, 2495;
28. (g) Bajwa, J.S.; Vivelo, J.; Slade, J.; Repic, O.; Blacklock, T. Selective Deprotection of Alkyl t-Butyldimethylsilyl Ethers in the Presence of Aryl t-Butyldimethylsilyl Ethers with Bismuth Bromide. Tetrahedron Lett. 2000, 41, 6021;
29. (h) Gopinath, R.; Patel, B.K. Tetrabutylammonium Tribromide (TBATB)-MeOH: An Efficient Chemoselective Reagent for the Cleabage of tert-Butyldimethylsilyl (TBDMS) Ethers. Org. Lett. 2000, 2, 4177;
30. (i) Amkala, S.V.; Fenteany, G. Selective Deprotection of Either Alkyl or Aryl Silyl Ethers from Aryl, Alkyl bis-Silyl Ethers. Tetrahedron Lett. 2002, 43, 4729;
31. (j) Yadav, J.S.; Reddy, B.V.S.; Madan, C. A Mild and Selective Cleavage of tert-Butyldimethylsilyl Ethers by Indium(III) Chloride. New J. Chem. 2000, 24, 853.
32. Maiti, G.; Roy, S.C. A Mild and Efficient Method for the Selective Cleavage of tert-Butyldimethylsilyl Ethers to Alcohols. Tetrahedron Lett. 1997, 38, 495.
33. (a) Lewis, A.; Stefanuti, I.; Swain, S.A.; Smith, S.A.; Taylor, R.J.K. Carbohydrate-based Routes to Salicylate Natural Products: Formal Total Synthesis of (+)-Apicularen A from D-Glucal. Tetrahedron Lett. 2001, 42, 5549;
34. (b) Hacsell, U.; Daves, G.D., Jr. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. Prog. Med. Chem. 1985, 22, 1;
35. (c) Evans, D.A.; Dinsmore, C.J.; Ratz, A.M.; Evrad, D.A.; Barrow, J.C. Synthesis and Conformational Properties of the M(4-6)(5-7) Bicyclic Tetrapeptide Common to the Vancomycin Antibiotics. J. Am. Chem. Soc. 1997, 119, 3417.
36. R) Catalysis in Synthesis. Synthesis 1986, 513.
37. (a) Olah, G.A.; Mathew, T.; Prakash, G.K.S. Nafion-H Catalysed Sulfonylation of Aromatics with Arene/Alkenesulfonic Acids for the Preparation of Sulfones. Chem. Commun. 2001, 2034;
38. (b) Nagai, H.; Kawahara, K.; Matsumura, S. Novel Stereocontrolled α- and β-Glycosidations of, Mannopyranosyl Sulfoxides Using Environmentally Benign Heterogeneous Solid Acids. Tetrahedron, Lett. 2001, 42, 4159.
39. (a) Kumareswaran, R.; Pachamuthu, K.; Vankar, Y.D. General synthetic methods. Part 13. Nafion-H Catalyzed Acetylation of Alcohols. Synlett. 2000, 1652;
40. (b) Gupta, A.; Vankar, Y.D. Transformations in-Carbohydrate Chemistry 1. Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-Valerolactones from C-2-Acetoxymethyl Glycals. Tetrahedron 2000, 56, 8525;
41. 4 (or Nafion-H) Catalysed Ionic Diels-Alder Reactions of Chiral and Achiral Olefinic Acetals Respectively. Tetrahedron 1999, 55, 1099.
42. Only phenolic TBDMS ethers needed heating at 50°C (cf. Entries 9 and 12 Table 1).
43. (a) Allerga, G.; Wilson, G.E., Jr.; Beneditti, E.; Pedone, C.; Albert, R. Structure of a Halosulfonium Salt. The 1:1 Adduct of Thiophane with Bromine. J. Am. Chem. Soc. 1970, 92, 4002;
44. (b) Furukawa, N.; Inoue, T.; Aida, T.; Oae, S. Preparation of Alkyl Bromides from the Corresponding Alcohols and Dimethylbromosulfonium Bromide. J. Chem.. Soc. Chem. Commun. 1973, 212.
45. (a) Olah, G.A.; Vankar, Y.D.; Arvanaghi, M.; Prakash, G.K.S. Synthetic Methods and Reactions; 69. Dethioacetalization with Bromodimethylsulfonium Bromide. Synthesis 1979, 720;
46. (b) Olah, G.A.; Vankar, Y.D.; Arvanaghi, M. Synthetic Methods and Reactions; 70. Oxidation of Thiols to Disulfides with Bromodimethylsulfonium Bromide. Synthesis 1979, 721;
47. (c) Olah, G.A.; Vankar, Y.D.; Arvanaghi, M. Synthetic Methods are Reactions. 73. Conversion of Epoxides and Enamines into α-Haloketones with Halodimethylsulfonium Halides. Tetrahedron Lett. 1979, 3653.
48. For other uses see (d) Chow, Y.L.; Bakker, B.H. Electrophilic Addition of Bromodimethylsulfonium Bromide to Olefins. Synthesis 1982, 648 and references cited therein;
49. (e) Majetich, G.; Hicks, R.; Reister, S. Electrophilic Aromatic Bromination Using Bromodimethylsulfonium Bromide Generated in situ. J. Org. Chem. 1997, 62, 4321.
50. Lee, A.S.-Y.; Yeh, H.-C.; Shie, J.-J A Novel, Highly Efficient and Selective Desilylating Method for Trialkylsilyl Ethers. Tetrahedron Lett. 1998, 39, 5249.
51. 2: C, 61.90; H, 9.84%. Found: C, 61.93, H, 9.81%.