Applications of trivalent and pentavalent tantalum in organic synthesis

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 43, Issue 4, 2004, Pages 813-838

  Chandrasekhar, Srivari ^a   Ramachandar, Tokala ^b   Shyamsunder, Tokala ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b TEMPLE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKENE; ALKYNE DERIVATIVE; ALLYL ALCOHOL; CARBOXYLIC ACID DERIVATIVE; FURAN DERIVATIVE; ISOCYANIC ACID DERIVATIVE; LEWIS ACID; NAPHTHOL DERIVATIVE; SULFIDE; TANTALUM;

ACYLATION; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHLORINATION; COMPLEX FORMATION; DEGRADATION; DEPROTECTION REACTION; DIELS ALDER REACTION; OXIDATION; REACTION ANALYSIS; REDUCTION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 2342636444     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (92)

1. Burdett K & Hughbanks T, J Am Chem Soc, 106, 1984, 3101.
2. Masuda T, Takahashi T & Higashimura T, J Chem Soc Chem Commun, 1982, 1297.
3. Sommer J, Nouv J Chim, 6, 1982, 3.
4. Hartung J B Jr & Pedersen S F, J Am Chem Soc, 111, 1989, 5468.
5. Fredericks S & Thomas J L, J Am Chem Soc, 100, 1978, 350.
6. Williams A C, Sheffels P, Sheehan D & Livinghouse T, Organometallics, 8, 1989, 1566.
7. LaPointe R E & Wolczanski P T, J Am Chem Soc, 108, 1986, 3535.
8. LaPointe R E, Wolczanski P T & Mitchell J F, J Am Chem Soc, 108, 1986, 6382.
9. Labiager J A, Schwartz J & Townsend J M, J Am Chem Soc, 96, 1974, 4009.
10. Smith G, Schrock R R, Churchill M R & Youngs W, J Inorg Chem, 20, 1981, 387.
11. Cotton F A & Hall W T, J Am Chem Soc, 101, 1979, 5094.
12. Cotton F A & Hall W T, Inorg Chem, 19, 1980, 2352.
13. Cotton F A & Hall W T, Inorg Chem, 19, 1980, 2354.
14. Cotton F & Roth W J, Inorg Chim Acta, 85, 1984, 17.
15. Katako Y, Miyai J, Tezuka M & Takai K, Tetrahedron Lett, 31, 1990, 389.
16. Takai K, Kataoka Y & Utimoto K, J Org Chem, 55, 1990, 1707.
17. Takai K, Miyai J, Kataoka Y & Utimoto K, Organometallics, 9, 1990, 3031.
18. Ichinose Y, Nozaki K, Wakamatsu K, Oshima K & Utimoto K, Tetrahedron Lett, 28, 1987, 3709.
19. Recht J, Cohen B I, Goldman A S & Kolm J, Tetrahedron Lett, 31, 1990, 7281.
20. Viard B, Poulain M, Grandjean D & Amaudrut J, J Chem Res, 1983, (S), 84.
21. Van Wagenen B C & Livinghouse T, Tetrahedron Lett, 30, 1989, 3495.
22. Wilkins J W, J Organomet Chem, 65, 1974, 383.
23. Wilkins J W, J Organomet Chem, 67, 1974, 289.
24. Wilkins J W, J Organomet Chem, 80, 1974, 349.
25. Takai K, Kataoka Y, Yoshizumi K, Oguchi Y & Utimoto K, Chem Lett, 1991, 1479.
26. Kataoka Y, Oguchi Y, Yoshizumi K, Miwatashi S, Takai K & Utimoto K, Bull Chem Soc Jpn, 65, 1992, 1543.
27. nd Edn, (McGraw-Hill Kogakusha Ltd, New York) 1977, 393.
28. Sugasawa S & Nakai S, Reactions Index of Organic Syntheses, (John Wiley, New York) 1967, 158.
29. Barnet J E G, Adv Carbohydr Chem, 22, 1967, 177
30. Helferich B, Chem Ber, 54, 1921, 1082.
31. Khan R, Adv Carbohydr Chem Biochem, 33, 1976, 236.
32. Haines A H, Adv Carbohydr Chem Biochem, 33, 1976, 11.
33. Szarek W A, Adv Carbohydr Chem Biochem, 28, 1973, 225.
34. Rydon H N & Tonge B L, J Chem Soc, 1956, 3043.
35. Coe E M & Jones C J, Polyhedron, 11, 1992, 3123.
36. Olah G A, Surya Prakash G K & Sommer S, Super-Acids, (Wiley, New York) 1985.
37. Vogel P, Carbocation Chemistry (Elsevier, Amsterdam) 1985.
38. Sommer S, Muller M & Laali K, New J Chem, 6, 1982, 3.
39. Siskin & Porcelli J, J Am Chem Soc, 96, 1974, 36.
40. Solari E, Floriani C, Chiesi-Villa A & Guast C, J Chem Soc Chem Commun, 1989, 1747.
41. Solari E & Schenk C K, J Chem Soc Chem Commun, 1990, 963.
42. Solari E, Floriani C, Chiesi-Villa A & Rizzoli C, J Chem Soc Chem Commun, 1991, 841.
43. Harada, The Chemistry of the Carbon-Nitrogen Double Bond, edited by S Patai (Interscience, London) 1970, Chap 6.
44. Ender D, Schubert H & Nübling, Angew Chem Int Ed Engl, 25, 1986, 1109.
45. Claremon D A, Lumma P K & Phillips B T, J Am Chem Soc, 108, 1986, 8265.
46. Denmark S E, Weber T & Piotrowski D W, J Am Chem Soc, 109, 1987, 2224.
47. Cohen S A & Bercaw J E, Organometallics, 4, 1985, 1006.
48. Buchwald S L, Watson B T & Huffman J C, J Am Chem Soc, 109, 1987, 2544.
49. Strickler J R & Wigley D E, Organometallics, 9, 1990, 1665.
50. Takai K, Miwatashi S, Kataoka Y & Utimoto K, Chem Lett, 1992, 99.
51. Hudlicky M, Reductions in Organic Chemistry (Wiley, New York) 1984.
52. Kataoka Y, Takai K, Oshima K & Utimoto K, J Org Chem, 57, 1992, 1615.
53. Buchwald S L, Lum R T & Dewan J C, J Am Chem Soc, 108, 1986, 7441.
54. Takahashi T, Swanson D R & Negishi E, Chem Lett, 1987, 623.
55. Negishi E, Holmes S J, Tour J M, Miller J A, Cederbaum F E, Swanson D R & Takahashi T, J Am Chem Soc, 111, 1989, 3336.
56. Wilkins J D, J Organomet Chem, 67, 1974, 269.
57. Kataoka Y, Tezuka M, Takai K & Utimoto K, Tetrahedron, 48, 1992, 3495.
58. Buchwald S L, Watson B T, Wannamaker M W & Dewan J C, J Am Chem Soc, 111, 1989, 4486.
59. Grossman R B, Davis W M & Buchwald S L, J Am Chem Soc, 113, 1991, 2321.
60. Jensen M & Livinghouse T, J Am Chem Soc, 111, 1989, 4495.
61. Sumrell G, J Org Chem, 19, 1954, 817.
62. Compounds having carbon-nitrogen double bonds, such as imines and oximes were unreactive toward tantalum-alkyne complexes. Insertion of a carbon-nitrogen triple bond into a tantalum-alkyne complex, see Strickler J R & Wigley D E, Organometallics, 9, 1990, 1665.
63. LaPointe R E, Wolczanki P T & Van Duyne G D, Organometallics, 4, 1985, 1810.
64. Arney D J, Bruck M A & Wigley D E, Organometallics, 10, 1991, 3947.
65. Takai K, Odaka H, Kataoka Y & Utimoto K, Tetrahedron Lett, 35, 1994, 1893.
66. Rathke M W, Organic Reactions: The Reformatsky Reaction, edited by W G Dauben (Wiley, New York) 1975, 423.
67. Aoyagi Y, Tanaka W & Ohta A, J Chem Soc Chem Commun, 1994, 1225.
68. Takai K, Yamada M, Odaka H & Utimoto K, J Org Chem, 1994, 5852.
69. Eisch J J, J Organomet Chem, 200, 1980, 101.
70. Normant J F & Alexakis A, Synthesis, 1981, 141.
71. Vara Prasad J V N & Pillai C N, J Orgnomet Chem, 259, 1983, 1.
72. Hoveyda A H, Evans D A & Fu G C, Chem Rev, 93, 1993, 1307.
73. Cherest M, Felkin H, Frajerman C, Lion C, Roussi G & Swierczewski G, Tetrahedron Lett, 1966, 875.
74. Felkin H, Swierczewski G & Tambute A Tetrahedron Lett, 1969, 707.
75. Harris T V, Coleman R A, Dickson R B & Thompson D W, J Organomet Chem, 3, 1977, 239.
76. Hoveyda A H & Xu Z, J Am Chem Soc, 113, 1991, 5079.
77. Takai K, Yamada M, Odaka H, Utimoto K, Fuji T & Furukawa I, Chem Lett, 1995, 315.
78. Takai K, Yamada M, Odaka H & Utimoto K, Chem Lett, 1995, 851.
79. Maeta H, Nagasawa T, Handa Y, Takei T, Osamura Y & Suzuki K, Tetrahedron Lett, 36, 1995, 899.
80. Sakurai H, Pure and Appl Chem, 57, 1985, 1759.
81. Chandrasekhar S, Mohanty P M & Raza A, Synth Commun, 29, 1999, 257.
82. Howarth J & Gillespie K, Tetrahedron Lett, 37, 1996, 6011.
83. Chandrasekhar S, Takhi M & Uma G, Tetrahedron Lett, 38, 1997, 8089.
84. Chandrasekhar S, Padmaja M B & Raza A, Synlett, 1999, 1597.
85. Chandrasekhar S, Takhi M, Reddy Y R, Mohapatra S, Rao C R & Reddy K V, Tetrahedron, 1997, 14997.
86. Prins H, J Chem Weekl, 16, 1919, 1072
87. Adams D R & Bhatnagar S P, Synthesis, 1997, 661.
88. Chandrasekhar S & Reddy B V S, Synlett, 1998, 651.
89. Chandrasekhar S, Prakash S J, Jagadeshwar V & Narsihmulu Ch, Tetrahedron Lett, 42, 2001, 5561.
90. Qian C & Huang T, J Org Chem, 63, 1998, 4125.
91. Chandrasekhar S, Ramachandar T & Takhi M, Tetrahedron Lett, 39, 1998, 3263.
92. Chandrasekhar S, Ramachandar T & Prakash S J, Synthesis, 2000, 1817.