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64549090384
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Reviews
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Reviews:
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0345979435
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Ulman A. Chem. Rev. 96 (1996) 1533-1554
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7
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Lahann J., Mitragotri S., Tran T.N., Kaide H., Sudaram J., Choi I.S., Hoffer S., Somorjar G.A., and Langer R. Science 299 (2003) 371-374
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Science
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Lahann, J.1
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Basabe-Desmonts L., Beld J., Zimmerman R.S., Hernando J., Mela P., Parajo M.F.G., Van Hulst N.F., Berg A.V.D., Reinhouldt D.N., and Crego-Calama M. J. Am. Chem. Soc. 126 (2004) 7293-7299
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Parajo, M.F.G.6
Van Hulst, N.F.7
Berg, A.V.D.8
Reinhouldt, D.N.9
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Hamelmann F., Heinzmann U., Siemeling U., Bretthauer F., and vor der Briiggen J. Appl. Sur. Sci. 222 (2004) 1-5
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vor der Briiggen, J.5
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Nguyen T.B., Castanet A.S., Nguyen T.H., Nguyen K.P.P., Bardeau J.F., Gibaud A., and Mortier J. Tetrahedron 62 (2006) 647-651
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Tetrahedron
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Recent review
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Recent review:
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64549144342
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4 are efficient catalysts for cross-coupling reactions of phenyltrimethylsilylacetylene with acyl chlorides and aryl triflates, respectively. Both reactions presumably involve CuCl promoted Si-C(sp) bond cleavage of the alkynylsilane to form an alkynylcopper species with high reactivity toward coupling with the electrophiles and transmetalation giving an alkynylpalladium species leads to the smooth catalytic reactions. See:
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4 are efficient catalysts for cross-coupling reactions of phenyltrimethylsilylacetylene with acyl chlorides and aryl triflates, respectively. Both reactions presumably involve CuCl promoted Si-C(sp) bond cleavage of the alkynylsilane to form an alkynylcopper species with high reactivity toward coupling with the electrophiles and transmetalation giving an alkynylpalladium species leads to the smooth catalytic reactions. See:
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0034708636
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Nishihara Y., Ikegashira K., Hirabayashi K., Ando J., Mori A., and Hiyama T. J. Org. Chem. 65 (2000) 1780-1787
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Nishihara, Y.1
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Hiyama, T.6
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64549103109
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Eur. Pat. Appl. EP 351092
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Tamura, H.; Ogawa, K. Eur. Pat. Appl. EP 351092, 1990;
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Tamura, H.1
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64549157335
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Ogawa, K. Eur. Pat. Appl. EP 339677, 1989.
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(1989)
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Ogawa, K.1
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64549092558
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note
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Trichloro[ω-(trimethylsilyl)alkynyl]silanes with an odd number of carbons are comparatively more expensive to produce since relatively expensive reactants are required to obtain the same.
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0030697219
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Srisiri W., Lee Y.S., Sisson T.M., Bondurant B., and O'Brien D.F. Tetrahedron 53 (1997) 15397-15414
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Tetrahedron
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0001651665
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Synth. Commun.
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36
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Perchonock C.D., Uzinskas I., McCarthy M.E., Erhard K.F., Gleason J.G., Wasserman M.A., Muccitelli R.M., DeVan J.F., Tucker S.S., Vickery L.M., Kirchner T., Weichman B.M., Mong S., Scott M.O., Chi-Rosso G., Wu H.L., Crooke S.T., and Newton J.F. J. Med. Chem. 29 (1986) 1442-1452
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Newton, J.F.18
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39
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2442497333
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Bis-alkynylation is obtained in the presence of 3 equiv of the Grignard reagent under similar conditions
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Yang L.M., Huang L.F., and Luh T.Y. Org. Lett. 6 (2004) 1461-1463 Bis-alkynylation is obtained in the presence of 3 equiv of the Grignard reagent under similar conditions
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Org. Lett.
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Yang, L.M.1
Huang, L.F.2
Luh, T.Y.3
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note
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Hence, for n=10, the retention factors of 9b, 6b, and 11b are, respectively, 0.38, 0.33, and 0.28 (hexane/ethylacetate 9:1).
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41
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