α-Trifluoromethylated carbanion synthons

Accounts of Chemical Research

Volumn 41, Issue 7, 2008, Pages 817-829

  Uneyamaz, Kenji ^a   Katagiri, Toshimasa ^a   Amii, Hideki ^b  

^a OKAYAMA UNIVERSITY   (Japan)

^b KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 49049116516     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar7002573     Document Type: Article

References (98)

1. Prakash, G. K. S.; Mandal, M. Nucleophilic trifluoromethylation. J. Fluorine Chem. 2001, 112, 123-131.
2. Langlois, B. R.; Billard, T.; Roussel, S. Nucleophilic trifluoromethylation, some recent reagents and their stereoselective aspects. J. Fluorine Chem. 2005, 126, 173-179.
3. Ma, J.-A.; Cahard, D. Asymmetric fluorination, trifluoromethylation and perfluoroalkylation reactions. Chem. Rev. 2004, 104, 6119-6146.
4. McClinton, M. A.; McClinton, D. A. Trifluoromethylations and related reactions in organic chemistry. Tetrahedron 1992, 48, 6555-6666.
5. Sandford, G. Perfluoroalkanes. Tetrahedron 2003, 59, 437-454.
6. Culkin, D. A.; Hartwig, J. F. Trifluoroethyl p-tolyl palladium species is known to be stable and it undergoes reductive elimination on heating at 110°C leading to the formation of 2,2,2-trifluoro-1-tolylethane. Organometallics 2004, 23, 3398-3416.
7. Yamauchi, Y.; Kawate, T.; Katagiri, T.; Uneyama, K. Application of trifluoromethyl group stabilizing optically active oxiranyl and aziridinyl anions for stereospecific syntheses of trifluoromethylated compounds. Tetrahedron 2003, 59, 9839-9847.
8. Ishikawa, N.; Yokozawa, T. Convenient preparation of dimethyl (trifluoromethyl)malonate and related compounds. Bull. Chem. Soc. Jpn. 1983, 56, 724-726.
9. Fuchigami, T.; Nakagawa, Y. Electrolytic transformation of fluoroorganic compounds. 2. Generation and alkylation of a stable (trifluoromethyl)malonic ester enolate using an electrogenerated base. J. Org. Chem. 1987, 52, 5276-5277.
10. Komatsu, Y.; Sakamoto, T.; Kitazume, T. Synthetic applications of the carbanion with a fluoroalkyl group generated by palladium(0) catalyst under neutral conditions. J. Org. Chem. 1999, 64, 8369-8374.
11. Seebach, D.; Beck, A. K.; Renaud, P. Di- and trifluoro substituted dilithium compounds in organic syntheses. Angew. Chem., Int. Ed. Engl. 1986, 25, 98-99.
12. Uneyama, K.; Momota, M. Generation and chemical fate of 2,2,2-trifluoro-1-phenylsulfonylethyl carbanion. Bull. Chem. Soc. Jpn. 1989, 62, 3378-3379.
13. Qian, C.-P.; Nakai, T. Perfluoro-enolate chemistry: An "electrophile-coexisting" procedure for carbon-carbon bond forming reactions with an ester lithium-enolate. Tetrahedron Lett. 1990, 31, 7043-7046.
14. 3 enolate with fluoral. Org. Lett. 2003, 5, 4807-4809.
15. Nakamura, Y.; Uneyama, K. Fluoride ion-catalyzed 1,2-deslilylative defluorination: Syntheses of 1-substituted 2,2-difluorostyrenes. J. Org. Chem. 2007, 72, 5894-5897.
16. Gassman, P. G.; O'Reilly, N. J. (Pentafluoroethyl)lithium generation and use in synthesis. Tetrahedron Lett. 1985, 26, 5243-5246.
17. Uno, H.; Suzuki, H. Nucleophilic perfluoroalkylation using perfluoroalkyllithiums. Synlett 1993, 91-96.
18. Hemer, I.; Posta, A.; Dedek, V. Fluorohalogeno compounds. I. The Grignard reaction of some fluorohalogenoethanes. J. Fluorine Chem. 1984, 26, 467-479.
19. Fujita, M.; Hiyama, T. Efficient carbonyl addition of polyfluorochloroethyl,-ethylidene, and -ethenyl units by means of 1,1,1-trichloro-2,2,2-trifluoroethane and zinc. Bull. Chem. Soc. Jpn. 1987, 60, 4377-4384.
20. Yamauchi, Y.; Katagiri, T.; Uneyama, K. The first generation and stereospecific alkylation of α-trifluoromethyl oxiranyl anion. Org. Lett. 2002, 4, 173-176.
21. Yamauchi, Y.; Kawate, T.; Itahashi, H.; Katagiri, T.; Uneyama, K. Generation and reactions of α-trifluoromethyl stabilized aziridinyl anion, a general synthetic precursor for stereospecific construction of α-amino-α-trifluoromethylated quaternary carbon. Tetrahedron Lett. 2003, 44, 6319-6322.
22. Morken, P. J.; Lu, H.; Nakamura, A.; Burton, D. J. Convenient preparation and functionalization of 2-metallated pentafluoropropenes. Tetrahedron Lett. 1991, 32, 4271-4274.
23. Jiang, B.; Wang, Q.-F.; Yang, C.-G.; Xu, M. α-(Trifluoromethyl) ethenyl boronic acid as a useful trifluoromethyl containing building block. Preparation and palladium-catalysed coupling with aryl halides. Tetrahedron Lett. 2001, 42, 4083-4085.
24. Watanabe, H.; Yamashita, F.; Uneyama, K. Trifluoroacetimidoyl lithium; generation and reaction with electrophile. Tetrahedron Lett. 1993, 34, 1941-1944.
25. Watanabe, H.; Yan, F.-Y.; Sakai, T.; Uneyama, K. (Trifluoroacetimidoyl) lithiums and their reaction with electrophiles. J. Org. Chem. 1994, 59, 758-761.
26. Uneyama, K.; Noritake, C.; Sadamune, K. Generation and reaction of metal free trifluoroacetimidoyl carbanion. J. Org. Chem. 1996, 61, 6055-6057.
27. Hudrlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; ACS monograph 187; American Chemical Society: Washington D.C., 1995.
28. 2. J. Magn. Reson. 1969, 7, 370-373.
29. Katagiri, T. Unpublished data.
30. Takagi, J.; Takihana, R.; Kuwano, A.; Uneyama, K. Facile preparation of polyfluoroalkylated aldimines from polyfluoroalkanoic acids. Synthesis 2007, 1624-1628.
31. (a) OPh: Nakai, T.; Tanaka, K.; Ishikawa, N. Reaction of 2,2,2-trifluoroethoxy-and 2,2,2-trifluoroethylthiobenzene with lithium dialkylamides. The formation of phenylthioynamines. Chem. Lett. 1876, 1263-1266.
32. (b) SPh: Nakai, T.; Tanaka, K.; Setoi, H.; Ishikawa, N. A convenient preparation of arylthioynamines. Bull. Chem. Soc. Jpn. 1977, 50, 3069-3070.
33. (c) OR: Garayt, M. R.; Percy, J. M. A direct and useful route to difluoroacylsilanes and difluoroacylstannanes and their potential for the generation of structurally diverse difluoroketones. Tetrahedron Lett. 2001, 42, 6377-6380.
34. (d) OTs: Ichikawa, J.; Sonoda, T.; Kobayashi, H. A novel synthesis of 1,1-difluoroolefins from 1,1,1-trifluoroethyl p-toluenesulfonate via boron ate-complex. Tetrahedron Lett. 1989, 30, 1641-1644.
35. (e) Percy, J. M. Building Block Approaches to Aliphatic Organofluorine Compounds. In Organofluorine Chemistry; Chambers, R. D., Ed. Topics in Current Chemistry, 193; Springer-Verlag: Berlin, 1997.
36. (f) F: Kanai, M.; Percy, J. M. Short, stereoselective syntheses of α-fluoroalkenoate derivatives, α-fluoroenones and α-fluoroenals from HFC-134a. Tetrahedron Lett. 2000, 41, 2453-2456.
37. Yokozawa, T.; Nakai, T.; Ishikawa, N. (Trifluoromethyl)ketene silyl acetal as an equivalent to the trifluoropropionic ester enolate: Preparation and aldol-type reactions with acetals. Tetrahedron Lett. 1984, 25, 3987-3990.
38. Yokozawa, T.; Yamaguchi, M.; Nakai, T.; Ishikawa, N. The enol silyl ether of 3,3,3-trifluoropropiophenone preparation and carbon-carbon bond forming reactions. Nippon Kagaku Kaishi 1985, 2202-2204.
39. Ishihara, T.; Kuroboshi, M.; Yamaguchi, K.; Okada, Y. An efficient generation of the aluminum enolates of 1H-perfluoroalkyl ketones from 1-substituted-1-perfluoroalkenyl phosphates and their aldol reaction with aldehydes. J. Org. Chem. 1990, 55, 3107-3114.
40. Kuroboshi, M.; Ishihara, T. An efficient generation and selective aldol reaction of the boryl enolates of N N-dialkyl-2,3,3,3-tetrafluoropropanamides. Bull. Chem. Soc. Jpn. 1990, 63, 1191-1195.
41. 3 ketone: Theoretical study and high-yielding and diastereoselective aldol reaction. J. Am. Chem. Soc. 2004, 126, 13174-13175.
42. 3 ketones: Theoretical guideline, direct generation, and synthetic use. Chem. Rec. 2006, 6, 1-11.
43. Farnham, W. B. Fluorinated carbanions. Chem. Rev. 1996, 96, 1633-1640.
44. Henne, A. L.; Francis, W. C. Perfluorinated Grignard derivatives. J. Am. Chem. Soc. 1951, 73, 3518-3518.
45. Pierce, O. R.; McBee, E. T.; Judd, G. F. Preparation and reactions of (perfluoroalkyl)lithiums. J. Am. Chem. Soc. 1954, 76, 474-478.
46. Gassman, P. G.; O'Reilly, N. J. Nucleophilic addition of the pentafluoroethyl group to aldehydes, ketones, and esters. J. Org. Chem. 1987, 52, 2481-2490.
47. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Boron trifluoride-assisted reaction of (perfluoroalkyl)lithiums with imines. A novel route to perfluoroalkylated amines. Chem. Lett. 1988, 17, 729-732.
48. Uno, H.; Okada, S.; Suzuki, H. Preparation of perfluoroalkyl azaarenes with a (perfluoroalkyl)lithium-boron trifluoride system. Tetrahedron 1991, 47, 6231-6242.
49. Maruoka, K.; Shimada, I.; Akakura, M.; Yamamoto, H. Conjugate addition of (perfluoroalkyl)lithiums to α,β-unsaturated carbonyl substrates by complexation with aluminum tris(2,6-diphenylphenoxide). Synlett 1994, 847-848.
50. Solladié-Cavallo, A.; Suffert, J. Synthesis of optically pure perfluoroalkyl aryl carbinols. Synthesis 1985, 659-662.
51. Haszeldine, R. N.; Walaschewski, E. G. Perfluoroalkyl Grignard and Grignard-type reagents. III. Heptafluoro-n-propylzinc iodide. J. Chem. Soc. 1953, 3607-3610.
52. Sekiya, A.; Ishikawa, N. Reaction of heptafluoro-1-methylethylzinc iodide with halides and anhydrides of carboxylic acids. Chem. Lett. 1977, 6, 81-84.
53. Kitazume, T.; Ishikawa, N. Ultrasound-promoted selective perfluoroalkylation on the desired position of organic molecules. J. Am. Chem. Soc. 1985, 107, 5186-5191.
54. Santini, G.; Le Blanc, M.; Riess, J. G. Perfluoroalkylcalcium derivatives. Reactions with carbonyl compounds. J. Chem. Soc., Chem. Commun. 1975, 678-679.
55. Kitazume, T.; Ishikawa, N. Perfluoroalkylation with ultrasonic irradiation. Nippon Kagaku Kaishi 1984, 1725-1730.
56. Kitazume, T.; Ishikawa, N. Perfluoroalkyltin(IV) halides: A novel perfluoroalkylating agent for carbonyl compounds. Chem. Lett. 1981, 10, 1337-1338.
57. Tanaka, H.; Yamashita, S.; Katayama, Y.; Torii, S. Lead bromide/aluminum-promoted reductive addition of 1,1,1-trichloro-2,2,2- trifluoroethane (flon) to aldehydes. Chem. Lett. 1986, 15, 2043-2044.
58. Suda, M. Reaction of 1,1-difluorocyclopropanes with organolithium compounds. Tetrahedron Lett. 1980, 21, 4355-4358.
59. Shibuya, A.; Pietz, S.; Taguchi, T. Generation and reactions of difluorocyclopropyl anion. Tetrahedron Lett. 1997, 38, 5537-5540.
60. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. Preparation of trifluoromethyl and other perfluoroalkyl compounds with (perfluoroalkyl) trimethylsilanes. J. Org. Chem. 1991, 56, 984-989.
61. Watanabe, S.; Fujita, T.; Sakamoto, M.; Mino, Y.; Kitazume, T. Trifluoromethylation and pentafluoroethylation of terpenoid carbonyl compounds used in perfumery. J. Fluorine Chem. 1995, 73, 21-26.
62. Hoffmann-Röder, A.; Schweizer, E.; Egger, J.; Seiler, P.; Obst-Sander, U.; Wagner, B.; Kansy, M.; Banner, D. W.; Diederich, F. Mapping the fluorophilicity of a hydrophobic pocket: synthesis and biological evaluation of tricyclic thrombin inhibitors directing fluorinated alkyl groups into the P pocket. Chem. Med. Chem. 2006, 1, 1205-1215.
63. Kawano, Y.; Kaneko, N.; Mukaiyama, T. Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and imines with (perfluoroalkyl) trimethylsilane. Bull. Chem. Soc. Jpn. 2006, 79, 1133-1145.
64. 3/KF/Cu(I) system. Tetrahedron Lett. 1991, 32, 91-92.
65. (a) Singh, R. P.; Shreeve, J. M. Perfluoroalkylation of simple inorganic molecules: A one step route to novel perfluoroalkylated compounds. Chem. Commun. 2002, 1818-1819.
66. (b) Yagupolskii, Y. L.; Kirij, N. V.; Shevchenko, A. V.; Tyrra, W.; Naumann, D. Perfluoroalkylation of heterocumulenes with trimethyl(perfluoroalkyl)silanes in the presence of fluoride ions: Synthesis of perfluoroalkanesulfinyl amides from N-organylsulfinyl amines. Tetrahedron Lett. 2002, 43, 3029-3031.
67. (c) Grellepois, F.; Timoshenko, V. M.; Shermolovich, Y. G.; Portella, C. New three-step domino reaction, "Thiophilic addition-β-elimination of fluoride-[3,3] sigmatropic rearrangement": Synthesis of α-allylic and α,α-bis(allylic) α-trifluoromethyl dithioesters. Org. Lett. 2006, 8, 4323-4326.
68. Murphy-Jolly, M. B.; Lewis, L. C.; Caffyn, A. J. M. The synthesis of tris(perfluoroalkyl)phosphines. Chem. Commun. 2005, 4479-4480.
69. Kolomeitsev, A. A.; Kadyrov, A. A.; Szczepkowska-Sztolcman, J.; Milewska, M.; Koroniak, H.; Bissky, G.; Barten, J. A.; Roeschenthaler, G.-V. Perfluoroalkyl borates and boronic esters: New promising partners for Suzuki and Petasis reactions. Tetrahedron Lett. 2003, 44, 8273-8277.
70. Katagiri, T.; Uneyama, K. A chemistry of 2,3-epoxy-1,1,1- trifluoropropane. J. Fluorine Chem. 2000, 105, 285-293.
71. Katagiri, T.; Uneyama, K. Functional group transformations at α-carbon to trifluoromethyl group. In Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; ACS Symposium Series 911; American Chemical Society: Washington, DC, 2005; pp 318-341.
72. (a) Drakesmith, F. G.; Stewart, O. J.; Tarrant, P. The preparation and reactions of lithium derivatives of trifluoropropene and trifluoropropyne. J. Org. Chem. 1968, 33, 280-289.
73. (b) Hanzawa, Y.; Kawagoe, K.; Kimura, N.; Kobayashi, Y. Stereoselective synthesis of trifluoromethylated olefin and diene. Chem. Pharm. Bull. 1986, 34, 3953-5395.
74. Dolbier, W. R.; Burkholder, C. R.; Piedrahita, C. A. Fluorinated allenes: The syntheses of 1-fluoropropadiene, 1,1-difluoropropadiene and 1,1-difluoro-3-methyl-1,2-butadiene. J. Fluorine Chem. 1982, 20, 637-647.
75. Nadano, R.; Ichikawa, J. 1-(Trifluoromethyl)vinylation via oxirane or oxetane ring-opening: A facile synthesis of 4- or 5-hydroxy-functionalized 2-trifluoromethyl-1-alkenes. Synthesis 2006, 128-132.
76. Lu, H.; Friedrichi, H. B.; Burton, D. J. A facile route to tetrafluoroallene. J. Fluorine Chem. 1995, 75, 83-86.
77. Jiang, B.; Xu, Y. Trifluoroisopropenylzinc reagent as a useful α-(trifluoromethyl)ethenyl carbanion synthetic equivalent. Preparation and palladium-catalyzed coupling with aryl halides. J. Org. Chem. 1991, 56, 7336-7340.
78. Peng, S.; Qing, F.-L. Fluorine-containing optically active allylic alcohols: preparation and Claisen rearrangement as a new entry to highly functionalized fluorinated amino alcohol derivatives. J. Chem. Soc., Perkin Trans. 1999, 3345-3348.
79. Morioka, M.; Sasaki, M.; Morisaki, K.; Mori, S. Preparation of fluorine-containing α,β-unsaturated carboxylic acids from fluorohaloalkenes. Japan Kokai Tokkyo Koho 2001, JP 2001-288138; Chem. Abstr. 2001, 135, 288521.
80. 3-containing compounds. J. Org. Chem. 1996, 61, 3200-3204.
81. (a) Xu, Y.; Jin, F.; Huang, W. (Trifluoroisopropenyl)tributyltin as a novel α-(trifluoromethyl)ethenyl carbanion synthetic equivalent, preparation and its palladium-promoted coupling with acyl chlorides. J. Org. Chem. 1994, 59, 2638-2641.
82. (b) Ichikawa, J.; Fujiwara, M.; Okauchi, T.; Minami, T. Fluorine-directed Nazarov cyclizations. Part 2. Regioselective synthesis of 5-trifluoromethyl-2- cyclopentenones. Synlett 1998, 927-929.
83. Fuchikami, T.; Yamanouchi, A.; Ojima, I. An effective and convenient route to 5-(trifluoromethyl)-5,6-dihydrouracils and their thio derivatives. Synthesis 1984, 766-768.
84. Pan, P.-Q.; Liu, X.-X.; Deng, M.-Z. A novel and convenient synthetic method for producing (±)-(trifluoromethyl)styrenes. J. Fluorine Chem. 1999, 95, 167-170.
85. Hu, C.-M.; Hong, F.; Xu, Y.-Y. Synthesis of trifluoromethyl-substituted conjugated enynes including a fluorinated siccayne. J. Fluorine Chem. 1993, 64, 1-4.
86. Akamatsu, C.; Yamauchi, Y.; Kobayashi, T.; Ozeki, Y.; Takagi, J.; Amii, H.; Uneyama, K. An improved synthesis of fluorinated imidoylsilanes. Synthesis 2006, 1836-1840.
87. Kobayashi, T.; Nakagawa, T.; Amii, H.; Uneyama, K. Mg-promoted double silylation of trifluoroacetimidoyl chlorides. A new entry to the fluorinated dianion equivalents. Org. Lett. 2003, 5, 4297-4300.
88. Mae, M.; Amii, H.; Kenji Uneyama, K. First synthesis of 3,3-difluoroserine and cysteine derivatives via Mg(0)-promoted selective C-F bind cleavage of trifluoromethylimines. Tetrahedron Lett. 2000, 41, 7893-7896.
89. Tamura, K.; Yan, F.-Y.; Sakai, T.; Uneyama, K. Generation and reaction of (N-aryltrifluoroacetimidoyl)zinc halides. Bull. Chem. Soc. Jpn. 1994, 67, 300-303.
90. Watanabe, H.; Hashizume, Y.; Uneyama, K. Homologation of trifluoroacetimidoyl iodides by palladium-catalyzed carbonylation. An approach to α-amino perfluoroalkanoic acids. Tetrahedron Lett. 1992, 33, 4333-4336.
91. Amii, H.; Kishikawa, Y.; Kageyama, K.; Uneyama, K. Palladium-catalyzed tert-butoxycarbonylation of trifluoroacetimidoyl iodides. J. Org. Chem. 2000, 65, 3404-3408.
92. Uneyama, K.; Watanabe, H. Palladium-catalyzed coupling reactions of trifluoroacetimidoyl iodides with olefins and 1-alkynes. Tetrahedron Lett. 1991, 32, 1459-1462.
93. Amii, H.; Kohda, M.; Seo, M.; Uneyama, K. A novel route to the fluorinated diimines: carbon monoxide-promoted reductive homocoupling of fluorinated imidoyl iodides in the presence of a palladium catalyst. Chem. Commun. 2003, 1752-1753.
94. Isobe, M.; Takagi, J.; Katagiri, T.; Uneyama, K. Palladium-catalyzed chloroimination of imidoyl chlorides to a triple bond: an intramolecular reaction leading to 4-chloroquinolines, Org. Lett. 2008, in press (DOI: 10.1021/ol800512m).
95. Amii, H.; Kishikawa, Y.; Uneyama, K. Rh(I)-catalyzed couping cyclization of N-aryl trifluoroacetoimidoyl chlorides with alkynes: One-pot synthesis of fluorinated quiolines. Org. Lett. 2001, 3, 1109-1112.
96. Nagayama, K.; Shimizu, I.; Yamamoto, A. Oxidative addition of aryl and benzyl trifluoroacetates to zerovalent palladium complexes with two modes of C-O bond cleavage processes. Bull. Chem. Soc. Jpn. 1999, 72, 799-803.
97. Kakino, R.; Shimizu, I.; Yamamoto, A. Synthesis of trifluoromethyl ketones by palladium-catalyzed cross-coupling reaction of phenyl trifluororacetate with organoboron compounds. Bull. Chem. Soc. Jpn. 2001, 74, 371-376.
98. Kashiwabara, T.; Kataoka, K.; Hua, R.; Shimada, S.; Tanaka, M. CO-Retentive addition reactions of fluorinated acid chlorides to alkynes. Org. Lett. 2005, 7, 2241-2244.