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1
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34047252983
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Dehydrogenative silylation of alcohols
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may be a more common designation in the field of organic synthesis
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"Dehydrogenative silylation of alcohols" may be a more common designation in the field of organic synthesis.
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2
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28244473021
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Some recent examples: a S. Rendler, G. Auer, M. Oestreich, Angew. Chem., Int. Ed. 2005, 44, 7620.
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Some recent examples: a) S. Rendler, G. Auer, M. Oestreich, Angew. Chem., Int. Ed. 2005, 44, 7620.
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3
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22344448563
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b) H. Ito, K. Takagi, T. Miyahara, M. Sawamura, Org. Lett. 2005, 7, 3001.
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(2005)
Org. Lett
, vol.7
, pp. 3001
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Ito, H.1
Takagi, K.2
Miyahara, T.3
Sawamura, M.4
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4
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18844408347
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c) H. Ito, A. Watanabe, M. Sawamura, Org. Lett. 2005, 7, 1869.
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(2005)
Org. Lett
, vol.7
, pp. 1869
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Ito, H.1
Watanabe, A.2
Sawamura, M.3
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5
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4143116942
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and references cited therein
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d) R. L. Miller, S. V. Maifeld, D. Lee, Org. Lett. 2004, 6, 2773, and references cited therein.
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(2004)
Org. Lett
, vol.6
, pp. 2773
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Miller, R.L.1
Maifeld, S.V.2
Lee, D.3
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6
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0001214450
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Selected reviews: a C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371.
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Selected reviews: a) C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371.
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7
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0000024039
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ed. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, Chap. 23, p
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b) D. Kost, I. Kalikhman, in The Chemistry of Organic Silicon Compounds, ed. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, 1998, Vol. 2, Chap. 23, p. 1339.
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(1998)
The Chemistry of Organic Silicon Compounds
, vol.2
, pp. 1339
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Kost, D.1
Kalikhman, I.2
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8
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0033603612
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3-catalyzed reaction of hydrosilanes with alcohols: a) J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887.
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3-catalyzed reaction of hydrosilanes with alcohols: a) J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887.
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9
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0033544810
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b) V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 8919.
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(1999)
Tetrahedron Lett
, vol.40
, pp. 8919
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Gevorgyan, V.1
Liu, J.-X.2
Rubin, M.3
Benson, S.4
Yamamoto, Y.5
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10
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0034703322
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c) V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179.
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(2000)
J. Org. Chem
, vol.65
, pp. 6179
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Gevorgyan, V.1
Rubin, M.2
Benson, S.3
Liu, J.-X.4
Yamamoto, Y.5
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11
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28944435691
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d) J. Chojnowski, S. Rubinsztajn, J. A. Cella, W. Fortuniak, M. Cypryk, J. Kurjata, K. Kázmierski, Organometallics 2005, 24, 6077.
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(2005)
Organometallics
, vol.24
, pp. 6077
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Chojnowski, J.1
Rubinsztajn, S.2
Cella, J.A.3
Fortuniak, W.4
Cypryk, M.5
Kurjata, J.6
Kázmierski, K.7
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12
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34047261554
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Compound la: colorless crystals (from hexane, mp 134-136°C. 1HNMR (benzene-d6, δ, 0.09 (br, 3H, 0.24 (br, 3H, 1.75-2.44 (br, 12H, 2.19 (s, 6H, 4.54 (sept, 3J, 4 Hz, 1H, 6.79 (br, 4H, 7.17 (ddd, 3J, 7 Hz, 3J, I Hz, 4J, 2 Hz, 1H, 7.24 (ddd, 3J, 7 Hz, 3J, 7 Hz, 4J, 2 Hz, 1H, 7.47 (d, 3J, 7 Hz, 1H, 7.56 (d, 3J, 7Hz, 1H, 13C{ 1H)NMR (CDCl3, δ, 2.9 (br, 21.25, 22.0-24.0 (br, 127.5-129.5 (br, 128.56, 128.97, 133.22, 134.31, 137.0-145.0 (br, 142.59, 156.7 (br, 11BNMR (THF-dg, δ) 75 (br, 29SiNMR (toluene-d8, δ, 18.0 (d of sept, 1Jsi-H, 193 Hz, 2Jsi-H, 7 Hz, MS(EI, m/z 384 (M, 34, 369 (M, Me, 99, 204 (100, IR KBr, cm
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2Si: C, 64.12; H, 8.84%. Found: C, 64.28; H, 9.04%.
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13
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34047265606
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The high solubility of the prepared alkoxy- and aminosilanes in common organic solvents lowered their isolated yields by recrystallization or precipitation. Precipitation from CH3CN was found to suppress loss of the products to as little as possible. However, the precipitate of 7 from CH3CN was contaminated with a small amount of by-products, which are under characterization. Pure 7 was obtained by recycling preparative HPLC in 30% yield
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3CN was contaminated with a small amount of by-products, which are under characterization. Pure 7 was obtained by recycling preparative HPLC in 30% yield.
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14
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34047245740
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Some recent examples of transition-metal-catalyzed reactions
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Some recent examples of transition-metal-catalyzed reactions:
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34047252452
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a) A. lida, A. Horii, T. Misaki, Y. Tanabe, Synthesis 2005, 2677.
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(2005)
Synthesis
, pp. 2677
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lida, A.1
Horii, A.2
Misaki, T.3
Tanabe, Y.4
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16
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0346789076
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b) K. Takaki, K. Komeyama, K. Takehira, Tetrahedron 2003, 59, 10381.
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(2003)
Tetrahedron
, vol.59
, pp. 10381
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Takaki, K.1
Komeyama, K.2
Takehira, K.3
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17
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0033612395
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c) K. Takaki, T. Kamata, Y. Miura, T. Shishido, K. Takehira, J. Org. Chem. 1999, 64, 3891.
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(1999)
J. Org. Chem
, vol.64
, pp. 3891
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Takaki, K.1
Kamata, T.2
Miura, Y.3
Shishido, T.4
Takehira, K.5
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18
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34047270350
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w(all data) = 0.2514, GOF = 1.065, T = 173 K (CCDC No. 632074).
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w(all data) = 0.2514, GOF = 1.065, T = 173 K (CCDC No. 632074).
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19
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0033555654
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Representative examples of Si-H⋯B intramolecular interaction: a B. Wrackmeyer, O. L. Tok, Y. N. Bubnov, Angew. Chem., Int. Ed. 1999, 38, 124.
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Representative examples of Si-H⋯B intramolecular interaction: a) B. Wrackmeyer, O. L. Tok, Y. N. Bubnov, Angew. Chem., Int. Ed. 1999, 38, 124.
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20
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0142087793
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b) B. Wrackmeyer, W. Milius, O. L. Tok, Chem.-Eur. J. 2003, 9, 4732.
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(2003)
Chem.-Eur. J
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, pp. 4732
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Wrackmeyer, B.1
Milius, W.2
Tok, O.L.3
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0347269069
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c) B. Wrackmeyer, O. L. Tok, Y. N. Bubnov, Appl. Organomet. Chem. 2004, 18, 43.
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(2004)
Appl. Organomet. Chem
, vol.18
, pp. 43
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Wrackmeyer, B.1
Tok, O.L.2
Bubnov, Y.N.3
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30544437225
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d) B. Wrackmeyer, O. L. Tok, W. Milius, A. Khan, A. Badshah, Appl. Organomet. Chem. 2006, 20, 99.
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(2006)
Appl. Organomet. Chem
, vol.20
, pp. 99
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Wrackmeyer, B.1
Tok, O.L.2
Milius, W.3
Khan, A.4
Badshah, A.5
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