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For an interesting example, see: a
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For an interesting example, see: (a) Yang, K. L.; Blackman, B.; Diederich, W.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Ahn, Y. M.; Georg, G. I. J. Org. Chem. 2003, 68, 10030-10039.
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Mossman, C.J.5
Roy, S.6
Ahn, Y.M.7
Georg, G.I.8
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(b) Lebreton, S.; Xie, X. S.; Ferguson, D.; De Brabander, J. K. Tetrahedron 2004, 60, 9635-9647.
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Lebreton, S.1
Xie, X.S.2
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8
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33749026617
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For a related discussion see: c
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For a related discussion see: (c) Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. Engl. 2006, 45, 6086-6101.
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Gradillas, A.1
Pérez-Castells, J.2
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12
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0000757151
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For a recent catalytic alkynylcupration-alkynylation of symmetrical arynes, see: For an inspiring example, see: a
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For an inspiring example, see: (a) Pansegrau, P. D.; Riecker, W. F.; Meyers, A. I. J. Am. Chem. Soc. 1988, 110, 7178-7184. For a recent catalytic alkynylcupration-alkynylation of symmetrical arynes, see:
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Pansegrau, P.D.1
Riecker, W.F.2
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(b) Xie, C.; Liu, L.; Zhang, Y.; Xu, P. Org. Lett. 2008, 12, 2393-2396.
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Corriu, R. J. P.; Guerin, C.; M'Boula, J. Tetrahedron Lett. 1981, 22, 2985-2986.
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Corriu, R.J.P.1
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M'Boula, J.3
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15
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(a) Ayalon-Chass, D.; Ehlinger, E.; Magnus, P. J. Chem. Soc., Chem. Commun. 1977, 772-773.
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Ayalon-Chass, D.1
Ehlinger, E.2
Magnus, P.3
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17
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0000611186
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For theoretical consideration of the high diastereoselectivity, see: c
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For theoretical consideration of the high diastereoselectivity, see: (c) Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 2582-2585.
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Fraenkel, G.1
Chow, A.2
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18
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0141847248
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For reviews see: a
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For reviews see: (a) Oshima, K. Sci. Synth. 2002, 4, 713-756.
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Oshima, K.1
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33646227616
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and references therein
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(b) Whitham, G. H. Sci. Synth. 2002, 4, 633-646, and references therein.
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Whitham, G.H.1
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21
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0037922749
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Palladium-catalysed carbon-carbon cross-coupling. Overview of the Negishi protocol with Zn, Al, Zr, and related metals
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Negishi, E.-I, Ed; John Wiley & Sons: New York
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(a) Negishi, E.-I. Palladium-catalysed carbon-carbon cross-coupling. Overview of the Negishi protocol with Zn, Al, Zr, and related metals. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed; John Wiley & Sons: New York, 2002; Vol. 1, pp 229-247.
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Handbook of Organopalladium Chemistry for Organic Synthesis
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Negishi, E.-I.1
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22
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0038675899
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Palladium-catalyzed cross-coupling substitution
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Negishi, E.-I, Ed, John Wiley & Sons: New York, and references therein
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(b) Negishi, E.-I., Dumond, Y. Palladium-catalyzed cross-coupling substitution. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons: New York, 2002; Vol. 1, pp 767-789, and references therein.
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Negishi, E.-I.1
Dumond, Y.2
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23
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61349128798
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2-Iodophenyl triflate 5 is converted to the corresponding aryne in the presence of 1.0 equiv of lithiated allyltrimethylsilane and 10 equiv of furan at -78 °C, affording 88% of the Diels-Alder cycloadduct.
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2-Iodophenyl triflate 5 is converted to the corresponding aryne in the presence of 1.0 equiv of lithiated allyltrimethylsilane and 10 equiv of furan at -78 °C, affording 88% of the Diels-Alder cycloadduct.
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24
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61349143415
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When the reaction is conducted with 3.0 equiv of lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, in the absence of the extra equivalent of lithiated allyltrimethylsilane under otherwise identical conditions, 8 is generated in 39% yield.
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When the reaction is conducted with 3.0 equiv of lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, in the absence of the extra equivalent of lithiated allyltrimethylsilane under otherwise identical conditions, 8 is generated in 39% yield.
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25
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61349150265
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Longer reaction times or lower temperatures have insignificant impact on yield
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Longer reaction times or lower temperatures have insignificant impact on yield.
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26
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61349096335
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Acetic acid could be added with comparable results
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Acetic acid could be added with comparable results.
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27
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0142109780
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Möller, M.; Husemann, M.; Boche, G. J. Organomet. Chem. 2001, 624, 47-52.
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31
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0141673219
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For a theoretical evaluation of relative energies of monosubstituted arynes, see
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For a theoretical evaluation of relative energies of monosubstituted arynes, see: Maurin, P.; Ibrahim-Ouali, M.; Parrain, J.-L.; Santelli, M. THEOCHEM 2003, 637, 91-100.
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Staamos, D.P.1
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Kishi, Y.3
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