Iodine in organic synthesis

Journal of Scientific and Industrial Research

Volumn 65, Issue 4, 2006, Pages 299-308

  Banerjee, Ajoy K ^a   Vera, William ^a   Mora, Henry ^a   Laya, Manuel S ^a   Bedoya, Liadis ^a   Cabrera, Elvia V ^b  

^a INSTITUTO VENEZOLANO DE INVESTIGACIONES CIENTÍFICAS   (Venezuela)

^b FACULTAD DE CIENCIAS VETERINARIAS   (Venezuela)

Author keywords

Cycloaddition; Esterification; Iodine; Organic synthesis

Indexed keywords

ACYLATION; ALDEHYDES; AROMATIZATION; CARBONYLATION; ESTERIFICATION; ETHERS; IODINE; KETONES; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL);

CHEMICAL PROCESS; IODINE; KETONE;

EID: 33645817713     PISSN: 00224456     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (69)

1. Frederickson M & Frederickson R, Electrophile mediated heteroatom cyclivation into c-c π bonds, Org Prep & Proc Int, 29 (1997) 33-62.
2. Bartlett P A, Stereocontrol in the synthesis of acyclic systems: applications to natural product synthesis, Tetrahedron, 36 (1980) 2-72.
3. Dowle M D & Davies D I, Chem Soc Rev, 8 (1979) 171-197.
4. Nicolaou K C & Sorensen E J, Classics in Total Synthesis (VCH, Weinheim, Germany) 1996, 65.
5. Pirrung M C, Morehead A T, Young B G, in Total Synthesis of Natural Products, vol 11, edited by D Goldsmith (John Wiley & Sons, New York) 2000, 148, 331, 336.
6. Badgar B P, Bettigeri S V & Joshi N S, Molecular iodine catalyzed highly rapid synthesis of 1,5-benzodiazopirane derivatives under mild conditions. Synth Commun, 34 (2004) 1447-1453.
7. Ramalinga K, Vijayalakshmi P & Kaimal T N B, A mild & efficient method for esterification & transesterification catalyzed by iodine, Tetrahedron Lett, 43 (2002) 879-882.
8. Yadav J S, Chand P K & Anjaneyulu S, Iodine-catalyzed allyction of aldehydes with trimetylsilane, Tetrahedron Lett, 43 (2002) 3783-3784.
9. Yadav J S, Reddy B V S, Rao C V & Rao K V, Elemental iodine catalyzed [4+2] cycloaddition reactions of O-quinomethanes: An efficient synthesis of trans-fused pyrano (3,2-c) benzopyranos., J Chem Soc, Perking I, (2002) 1401-1404.
10. Gordon P E & Fry A J, Hypophosphoranes acid-iodine: a novel reducing system reduction of benzhydrols to diaryl-methylene derivatives, Tetrahedron Lett, 42 (2001) 831-833.
11. Green T W & Wins P G M, Protective Groups in Organic Synthesis, 3rd edn (John Wiley & Sons, New York) 1999, 150-157.
12. Phukan P, Iodine as an extremely powerful catalyst for the acetylation of alcohols under solvent-free conditions, Tetrahedron Lett, 45 (2004) 4785-4787.
13. Larock R C, in Comprehensive Organic Transformations (VCH Publishers Inc., New York) 1989, 604-614.
14. Mukhopadahya C, Becker F F & Banik B K, A novel catalytic role of molecular iodine in the oxidation of benzylic alcohols: microwave assisted reaction, J Chem Res (S), (2001) 28-31.
15. Green T W, in Protective Groups in Organic Synthesis (John Wiley, New York) 1981, 129-133.
16. Samajdar S, Basu M K, Becker F F & Banik B K, A new molecular iodine catalyzed thioketalization of carbonyl compounds: Selectivity and scope, Tetrahedron Lett, 42 (2001) 4425-4427.
17. Firouzabadi H, Iranpoor N & Hazarkhani H, Iodine catalyzed efficient at chemoselective thioacetalization of carbonyl functions, transthioacetalizkion of O O & S, O cetals & acylals. J Org Chem, 66 (2001) 7527-7529.
18. Deka N & Sarma J C, Highly efficient dithioacetalization of carbonyl compounds catalyzed with iodine supported on neutral alkaline, Chem Lett, (2001) 794-795.
19. Zhang Y, Yu Y & Lin R, Samarium Triiodine catalyzed dithioacetal & dithioketal formation, Org Prep & Proc Int, (1993) 365-368.
20. Basu M K, Samajdar S, Becker F F & Banik B K, A new molecular iodine catalyzed acetalization of carbonyl compounds. Synlett, (2002), 319-321.
21. Karimi B & Golshani B, Iodine catalyzed efficient & mild procedure for highly chemoselective acetalization of carbonyl compounds under neutral aprotic conditions, Synthesis, (2002) 784-788.
22. Reddy M A, Reddy L R, Bhanumathi N & Rao K R, A mild and efficient method for tetrahydropyranolation and depyranolation of alcohols and phenols under neutral conditions, Synth Commun, 30 (2000) 4323-4328.
23. Deka N & Sarma J C, Microwave assisted catalytic protection & deprotection of alcohols with 3,4-dihydro-2H-pyran, Synth Commun, 30 (2000) 4435-441.
24. Deka N & Sarma J C, Microwave mediated selective monotetrahydropyranylation of symmetrical diols catalyzed by iodine, J Org Chem, 66 (2001) 1947-1948.
25. Yanada R, Bessho K & Yanada K, Metallic Samarium & iodine in alcohol. Selective 1,4 reduction of α, β-unsaturated carboxylic acid derivatives, Synlett, (1995) 443-444.
26. Wang L, Zhou L & Zhang Y, Reduction of aromatic nitro compounds using samarium metal in the presence of a catalytic amount of iodine under aqueous media, Synlett, (1999) 1065-1066.
27. Banik B K, Venkatraman M S, Mukhopadhyay C & Becker F F, A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine, Tetrahedron Lett, 39 (1998) 7243-7246.
28. Banik B K, Zegrocka O & Becker F F, Samarium-mediated iodine-catalyzed reductive amination of the adamantyl methyl ketone, J Chem Res (S), (2000) 321-323.
29. Banik B K, Zegrocka O, Banik I, Hackfield L & Becker F F, Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives, Tetrahedron Lett, 40 (1999) 6731-6734.
30. Ghatak A, Becker F F & Banik B K, Samarium-induced alkyl halide mediated reductive coupling of ketones, Tetrahedron Lett, 41 (2001) 3793-3796.
31. 2 system, Tetrahedron Lett, 39 (1998) 677-678.
32. Banerjee A K, Hurtado H, Laya M, Acevedo J & Alvarez J G, Total synthesis of (I) pisiferic acid, J Chem Soc Perkin Trans I, (1988) 931-938.
33. Banerjee A K, Peña-Matheud C A, Hurtado H E & Diaz M C, Synthesis of (±) 1β methoxy, 9β, 7β epoxy, 5α methoxy, trans decalin, Heterocycles, 24 (1986) 2155-2163.
34. Banerjee A K, Hurtado H E & Carrasco M C, Synthetic studies leading to the total synthesis of eudesmane sesquiterpenes. J Chem Soc, Perkins Trans I, (1982) 2547-2551.
35. Banerjee A K, González N C, Hernández S B & Fuentes S P, A formal total synthesis of (±)-Frullanolide, J Chem Res(S), (1990) 158-159.
36. Carrasco A K & Vera W, Synthetic studies on (I) Drimerin, J Chem Res(S), (1996) 108-109.
37. Banerjee A K, Synthesis of cyclic ethers & their utility in the synthesis of terpenoid compounds, J Sci Ind Res, 55 (1996) 915-930.
38. Kotnis A, A rapid entry to highly functionalized p-methoxy benzoates. Tetrahedron Lett, 31 (1990) 481-484.
39. Faulkner D J, Marine Natural reports, Natural Products Reports, 5 (1988) 613-663.
40. Tamura Y & Yoshimoto Y, An improved method for the conversion of cyclohexenones into anisoles, Chem Ind, (1980) 888-889.
41. Hedge S G, Kassim A M & Ingrum A I, Aromatization of cyclohexenones with iodine/sodium alkoxide. A Regioselective synthesis of 2-iodophenols, Tetrahedron Lett, 46 (1995) 8395-8398.
42. Horiuchi C A, Fukunishi H, Kajita M, Yamaguci A, Kiyomina H & Kiji S, New oxidative aromatization of α,β unsaturated cyclohexenones with Iodine Cerium (IV) Ammonium Nitrate in Alcohol, Chem Lett, (1991) 1921-1924.
43. Banerjee A K, Cabrera E V & Azocar, J A, Iodine-methanol induced novel fragmentation of byciclic diones to anisole derivatives, Synth Commun, 30 (2000) 3815-3821.
44. Phukan P, Iodine as a very powerful catalyst for three component synthesis of protected homoallylic amines, J Org Chem, 69 (2004) 4005-4006.
45. Phukan P, Mukaiyama aldol reactions of silyl enolates catalyzed by iodine, Synth Commun, 34 (2004) 1065-1070.
46. Nishide K, Yokota K, Nakamura D, Sumiya T, Node M, Ueda M & Fuji K, A new entry for the deprotection of monothioacetals & dithioacetals: Silver nitrite - iodine system, Tetrahedron Lett, 34 (1993) 3425-3428.
47. Vaino A R & Szarek W A, A mild & efficient method for the deprotection of tert-butyldimetylsilyl ethers using iodine in methanol, Chem Commun, (1996) 2351-2352.
48. Vaino A R & Szarek W A, Iodine in methanol: a simple selective method for the cleavage of p-methoxybenzyl ethers, Synlett, (1995) 1157-1158.
49. Vatele J M, Iodine in dichloromethane a simple method for selective cleavage of phenyl ethers, Synlett, (2001) 1989-1991.
50. Bedekar A V, Nair K B & Soman R, New simple 1,2-Iodoacetoxylation of alkenes, Synth Commun, 24 (1994) 2299-2305.
51. Sanseverino A M & de Mattos M C S, An improved synthesis of β-iodo ethers & iodohydrins from alkenes, Synthesis, (1998) 1584-1585.
52. Horiuchi C A, Ikeda A, Kanamori M, Hosokawa H, Sugiyama T & Takahashi T T, A new synthesis of trans iodohydrins using iodine cerium salt, J Chem Res(S), (1997) 60-61.
53. Noda Y & Kashima M, An efficient & regioselective direct aromatic iodination using iodine & nitrogen dioxide, Tetrahedron Lett, 38 (1997) 6225-6228.
54. Bonesi S M & Erra-Balsells R, Synthesis & isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide & N-iodosuccinimide-silica gel system, J Het Chem, 38 (2001) 77-87.
55. Lulinski P & Shulski L, Iodination of both deactivated & activated arenes with sodium per iodate or sodium iodate as the oxidants, Bull Chem Soc Jpn, 73 (2000) 951-956.
56. Lulinski P & Shulski L, Oxidative iodination of arenes with manganese (IV) oxide or potassium permanganate as the oxidants, Bull Chem Soc Jpn, 72 (1999) 115-120.
57. 2, Synthesis, (2003) 335-336.
58. Karimi B & Zareyee D, N-bromo succinimide & iodine catalyzed highly efficient deoxygenation of sulfoxides to thioethers using 3-mercaptopropionic acid under mild reaction conditions, Synthesis, (2003) 1875-1877.
59. Firouzabadi H, Iranpoor N & Sobhani S, A highly yielding preparation of a-trimethylsilyloxy phosphonates by silylation of α-hydroxyphosphonates with HMDS catalyzed by iodine, Tetrahedron Lett, 43 (2002) 3653-3655.
60. Capaccio C A I & Varela O, Stereocontrolled Diels-Alder cycloadditions of sugar-derived dihydropyranones, J Org Chem, 67 (2002) 7839-7846.
61. Yadav J S, Reddy B V S, Rao C V, Chand P K, & Prasad A R, Iodine-catalyzed stereoselective synthesis of allylglycosides, glycosyl cyanides & glycosyl azides, Synlett, (2001) 1638-1640.
62. Karimi B & Golshami B, Mild & highly efficient method for the sylalation of alcohols using hexamethil disilane catalyzed by iodine under nearly neutral reaction conditions, J Org Chem, 65 (2000) 7228-7230.
63. Yadav J S, Reddy B V S, Sadasiv K & Satheesh G, 1, 4-Conjugate addition of allyltrimethylsilane to α,β unsaturated ketones, Tetrahedron Lett, 43 (2002) 9695-9697.
64. Banik B K, Samajdar S & Banik I, Simple synthesis of substituted pyrroles, J Org Chem, 69 (2004) 213-216.
65. Xo X & Zhang Y, Synthesis of 3H-pyroles promoted by samarium/cat. Iodine system, Synth Commun, 32 (2002) 2643-2650.
66. Wang S-Yi, Molecular Iodine, Synlett, (2004) 2642-2643.
67. House H O, Modern Synthetic Reactions (W A Benjamin, California) 1972, 423,428,482.
68. Mundy B P & Ellerd M G, Name Reactions & Reagents in Organic Synthesis (John Wiley & Sons, New York) 1988, 372-373.
69. Clayden J P, Greeves N, Waren S & Wothers P D, Organic Chemistry (Oxford, London) 2002, 517-518, 882.