Katalityczne hydroborowanie

Meller, Jerzy; Zaidlewicz, Marek

Powiadomienia systemowe

Sesja wygasła!

Artykuł - szczegóły

Tytuł artykułu

Katalityczne hydroborowanie

Autorzy

Meller Jerzy , Zaidlewicz Marek

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Catalytic hydroboration

Języki publikacji

Abstrakty

Catalytic hydroboration a rapidly expanding branch of hydroboration reaction, is reviewed. Catecholborane is the hydroborating agent most often used in catalytic hydroboration. Rhodium, iridium, ruthenium, palladium and other transition metal compounds, including lanthanide iodides, are used as catalysts. The mechanism of catalytic hydroboration is discussed and schemes showing the catalytic action of Wilkinson's catalyst and lanthanide complexes are presented. The reactivity of alkenes in catalytic hydroboration decreases with the increasing substitution of the double bond. Generally, regioselectivities of the catalyzed and uncatalyzed hydroboration of terminal alkenes and alkynes are similar, the boron atom being placed preferentially at the terminal position. The catalyzed reaction makes possible higher selectivity by proper choice of the catalyst. However, the catalytic hydroboration of styrene and its derivatives may be directed to from preferentially the Markovnikov type addition products. Stereoselectivities of the catalyzed and incatalyzed hydroboration of allylic and homoallylic derivatives are often opposite. The catalytic monohydroboration of conjugated dienes and enynes provides the 1,2- and 1,4-additon products depending on the catalyst. Enantioselective catalytic hydroboration of prochiral olefins is described and selected reactions providing hydroboration to the synthesis of natural products are given.

Słowa kluczowe

hydroborowanie katalityczne

catalytic hydroboration

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

1999

Tom

[Z] 53, 11-12

Strony

787--809

Opis fizyczny

Bibliogr. 89 poz., wykr.

Twórcy

autor

Meller Jerzy

Zakład Chemii Organicznej, Wydział Chemii, Uniwersytet Mikołaja Kopernika, ul. J. Gagarina 7, 87-100 Toruń

autor

Zaidlewicz Marek

Zakład Chemii Organicznej, Wydział Chemii, Uniwersytet Mikołaja Kopernika, ul. J. Gagarina 7, 87-100 Toruń

Zakład Chemii Organicznej, Wydział Chemii, UMK, Toruń.

Bibliografia

[1] H. Brown, Hydroboration, Wiley-Intersdence, New York 1962.
[2] H. C. Brown, G. W. Kramer, A. B. Levy, M. M. Midland, Organic Syntheses via Boranes, Wiley-Interscience, New York 1975.
[3] A. Pelter, K. Smith, H. C. Brown, Boranc Reagents, Academic Press, New York 1988.
[4] H. C. Brown, S. K. Gupta, J. Am. Chem. Soc., 1975, 97, 5249.
[5] C. F. Lane, G. W. Kabalka, Tetrahedron, 1976, 32, 981.
[6] C. E. Tucker, J. Davidson, P. Knöchel, J. Org. Chem., 1992, 57, 3482.
[7] S. Pereira, M. Srebnik, Organometallics, 1995, 14, 3127.
[8] S. Pereira, M. Srebnik, J. Am. Chem. Soc., 1996, 118, 909.
[9] S. Pereira, M. Srebnik, Tetrahedron Lett., 1996, 37, 3283.
[10] A. Lang, H. Noth, M. Thomann-Albach, Chem. Ber., 1997, 130, 363.
[11] D. Männig, H. Noth, Angew. Chem. Int. Ed. Eng., 1985, 24, 878.
[12] K. Burgess, M. J. Ohlmeyer, Chem. Rev., 1991, 91, 1179.
[13] I. Beletskaya, A. Pelter, Tetrahedron, 1997, 53, 4957.
[14] K. Burgess, W. A. Van der Donk, Advanced Asymmetrie Synthesis, G. R. Stephenson Ed., Chapman and Hall, London 1996, s. 181.
[15] K. Burgess, W. A. Van der Donk, S. A. Westcott, T. B. Mander, R. T. Baker, J. C. Calabrese, J. Am. Chem. Soc, 1992, 114, 9350.
[16] S. A. Westcott, H. P. Blom, T. B. Marder, R. T. Baker, J. C. Calabrese, Inorg. Chem., 1993, 32, 2175.
[17] A T. Lynch, L. G. Sneddon, J. Am. Chem. Soc., 1987, 109, 5867.
[18] A. T. Lynch, L. G. Sneddon, ibid., 1989, 111, 6201.
[19] P. J. Fazen, L. G. Sneddon, Organometallics, 1994, 13, 2867.
[20] J. M. Brown, G. C. Lloyd-Jones, Tetrahedron: Asymmetry, 1990, 1, 869.
[21] K. Burgess, W. A. Van der Donk, M. J. Ohlmeyer, Tetrahedron: Asymmetry, 1991, 2, 613.
[22] J. R. Knorr, J. S. Merola, Organometallics, 1990, 9, 3008.
[23] D. A. Evans, G. C. Fu, J. Am. Chem. Soc., 1991, 113, 4042.
[24] D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc., 1992, 114, 6671.
[25] M. Satoh, Y. Nomoto, N. Miyaura, A. Suzuki, Tetrahedron Lett., 1989, 30, 3789.
[26] Y. Matsumoto, M. Naito, T. Hayashi, Organometallics, 1992, 11, 2732.
[27] E. K. Van den Beuken, N. Veldman, W. J. J. Smeets, A. L. Spek, B. L. Feringa, ibid., 1998, 17, 636.
[28] K. Burgess, M. Jaspars, ibid., 1993, 12, 4197.
[29] X. He, J. H. Hartwig, J. Am. Chem. Soc., 1996, 118, 1696.
[30] I. D. Gridnev, N. Miyaura, A. Suzuki, Organometallics, 1993, 12, 589.
[31] G. W. Kabalka, C. Narayana, N. K. Reddy, Synth. Commun., 1994, 24, 1019.
[32] M. Zaidlewicz, J. Meller, Tetrahedron Lett, 1997, 38, 7279.
[33] M. Zaidlewicz, J. Meller, Collect. Czech. Chem. Commun, 1999, 64, 1049.
[34] D. A. Evans, A. R. Muci, R. Stürmer, J. Org. Chem., 1993, 58, 5307.
[35] K. N. Harrison, T. J. Marks, J. Am. Chem. Soc., 1992, 114, 9220.
[36] E. A. Bijpost, R. Duchateau, J. H. Teuben, J. Mol. Catal. A: Chem., 1995, 95, 121.
[37] J. J. J. Juliette, I. T. Horvath, J. A Gładysz, Angew. Chem. Int. Ed. Engl., 1997, 36, 1610.
[38] D. A. Evans, G. C. Fu, J. Org. Chem, 1990, 55, 2280.
[39] K. Burgess, W. A. Van der Donk, A. M. Kook, ibid., 1991, 56, 2949.
[40] D. A. Evans, G. C. Fu, B. A. Anderson, J. Am. Chem. Soc., 1992, 114, 6679.
[41] D. G. Musaev, M. Mebel, K. Morokuma, ibid., 1994, 116, 10693.
[42] A. E. Dorigo, P. von Rague Schleyer, Angew. Chem. Int. Ed. Engl, 1995, 34, 115.
[43] H. Kono, K. I to, Y. Nagai, Chem. Lett., 1975, 1095.
[44] S. A. Westcott, T. J. Taylor, T. B. Marder, R. T. Baker, N. J. Jones, J. C. Calabrese, J. Chem. Soc., Chem. Commun., 1991, 304.
[45] S. A. Westcott, T. B. Marder, R. T. Baker, J. C. Calabrese, Can. J. Chem., 1993,71,930.
[46] S. A. Westcott, H. P. Blom, T. B. Marder, R. T. Baker, J. Am. Chem. Soc., 1992, 114. 8863.
[47] T. Hayashi, Y. Matsumoto, Y. Ito, ibid., 1989, 111, 3426.
[48] J. Zhang, B. Lou, G. Guo, L Dai, J. Org. Chem., 1991, 56, 1670.
[49] T. Hayashi, Y. Matsumoto, Tetrahedron: Asymmetry, 1991, 2, 601.
[50] M. P. Doyle, L. J. Westrun, M. N. Protopova, M. Y. Eismont, M. B. Jarstfer, Mendeleev Commun., 1993, 81.
[51] H. C. Brown, T. Hamaoka, N. Ravindran, J. Am. Chem. Soc., 1973, 95, 5786.
[52] H. C. Brown, T. Hamaoka, N. Ravindran, ibid., 1973, 95, 6456.
[53] N. Miyaura, A. Suzuki, J. Chem. Soc., Chem. Commun., 1979, 866.
[54] Y. Suseela, A. S. Bhanu Prasad, M. Periasamy, J. Chem. Soc., Chem. Commun., 1990, 446.
[55] A. Arase, M. Hoshi, A. Mijin, K. Nishi, Synth. Commun., 1995, 25, 1957.
[56] G. Zweifel, K. Nagase, H. C. Brown, J. Am Chem. Soc. 1962, 84, 183.
[57] H. C. Brown, R. Liotta, G. W. Kramer, J. Org. Chem., 1978, 43, 1058.
[58] G. Zweifel, K. Nagase, H. C. Brown, J. Am. Chem. Soc., 1962, 84, 190.
[59] M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, I. Denne, Tetrahedron Lett., 1987, 28, 4169.
[60] S. Elgendy, G. Patel, V. V. Kakkar, G. Claeson, D. Green, E. Skordalakes, J. A. Baban, J. Deadman, ibid., 1994, 35, 2435.
[61] D. S. Matteson, Acc. Chem. Res., 1988, 21, 294.
[62] D. S. Matteson, Chem. Rev., 1989, 89, 1535.
[63] X. L. Hou, D. G. Hong, G. B. Rong, Y. L. Guo, Tetrahedron Lett., 1993, 34, 8513.
[64] M. Hoshi, Y. Masuda, A. Arase, Bull. Chem. Chem. Soc. Jpn., 1990, 63, 447.
[65] K. Burgess, M. J. Ohlmeyer, Tetrahedron Lett., 1989, 30, 5857.
[66] K. Burgess, M. J. Ohlmeyer, J. Org. Chem., 1991, 56, 1027.
[67] K. Burgess, M. J. Ohlmeyer, ibid., 1991, 56, 1020.
[68] D. A Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc., 1988, 110, 6917.
[69] K. Burgess, M. J. Ohlmeyer, Tetrahedron Lett., 1989, 30, 5861.
[70] K. Burgess, W. A. Van der Donk, M. B. Jarstfer, M. J. Ohlmeyer, J. Am. Chem. Soc., 1991, 113, 6139.
[71] D. A. Evans, J. R. Gage, J. L. Leighton, ibid., 1992, 114, 9334.
[72] A. S. Kende, K. Liu, K. M. JosBrands, ibid., 1995, 117, 10597.
[73] D. L. Boger, T. Honda, ibid., 1994, 116, 5647.
[74] S. Hatakeyama, M. Kawamura, S. Takano, H. Irie, Tetrahedron Lett., 1994, 35, 7993.
[75] A. N. Hulme, S. S. Henry, A. I. Meyers, J. Org. Chem., 1995, 60, 1265.
[76] G. Hareau-Vittini, P. J. Kocienski, Synlett, 1995, 893.
[77] J. Cossy, S. BouzBouz, Tetrahedron Lett., 1996, 37, 5091.
[78] K. Burgess, M. J. Ohlmeyer, J. Org. Chem., 1988, 53, 5178.
[79] A. Suzuki, M. Sato, N. Miyaura, Tetrahedron Lett., 1990, 31, 231.
[80] J. M. Brown, D. I. Hulmes, T. P. Layzell, J. Chem. Soc. Chem. Commun., 1993, 1673.
[81] J. M. Valk, G. A. Whitlock, T. P. Layzell, J. M. Brown, Tetrahedron: Asymmetry, 1995, 6, 2593.
[82] K. Burgess, M. J. Ohlmeyer, K H. Whitmire, Organometallics, 1992, 11, 3588.
[83] A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc., 1994, 116, 4062.
[84] A. Schnyder, L. Hintermann, A Togni, Angew. Chem. Int. Ed. Eng., 1995, 34,
[85] A. Carmona, A. Corma, M. Iglesias, S. San Jose, F. Sanchez, J. Organomet. Chem., 1995, 492, 11.
[86] J. Spencer, V. Grämlich, R. Häusel, A. Togni, Tetrahedron: Asymmetry, 1996, 7, 41.
[87] H. C. L. Abbenhuis, U. Burckhardt, V Grämlich, A. Martelletti, J. Spencer, I. Steiner, A Togni, Organometallics, 1996, 15, 1614.
[88] A. Schnyder, A. Togni, U. Wiesli, ibid., 1997, 16, 225.
[89] T. Hayashi, Y. Matsumoto, Tetrahedron Lett., 1991, 32, 3387.

Uwagi

Opracowanie rekordu ze środków MNiSW, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2024).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS1-0005-0065