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For recent work, see: J. Barluenga, F. J. González-Bobes, M. C. Murguía, S. R. Ananthoju and J. M. González, Chem. Eur. J., 2004, 10, 4206.
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For recent examples, see for instance: (a) J. Barluenga, H. Vázquez-Villa, A. Ballesteros and J. M. González, J. Am. Chem. Soc., 2003, 125, 9028;
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For an example of unusual selectivity for the ortho-iodination in the aromatic substitution reaction, see: G. Espuña, G. Arsequell, G. Valencia, J. Barluenga, J. Alvarez-Gutiérez, A. Ballesteros and J. M. González, Angew. Chem. Int. Ed., 2004, 43, 325.
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18044388435
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note
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13C) spectroscopic and MS data. All new compounds 2 gave satisfactory elemental analysis and/or HRMS data, according to the proposed structures.
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25
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For an intermolecular arylation reaction of alkynes, see: (a) J. Barluenga, M. A. Rodríguez, J. M. González and P. J. Campos, Tetrahedron Lett., 1990, 31, 4207;
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4344659549
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(b) In a recent report using IC1, it was assumed that the iodoarylation processes should be applicable only to cyclize electron-rich and conjugated biaryl alkyne fragments, see: T. Yao, M. A. Campo and R. C. Larock, Org. Lett., 2004, 6, 2677. Clearly, this is not mandatory in our system, nor was it in our related previous work.
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For the preparation of related tetrasubstituted cycloalkenes and their use as precursors for the synthesis of cis-3,4-disubstituted chromanes upon hydrogenation, see: P. S. Bury, L. S. Christiansen, P. Jacobsen, A. S. Jørgensen, A. Kanstrup, L. Nærum, S. Bain, C. Fledelius, B. Gissel, B. S. Hansen, N. Korsgaard, S. M. Thorpe and K. Wassermann, Bioorg. Med. Chem., 2002, 10, 125.
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18044396401
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note
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This is a relevant characteristic in order to further apply this methodology to the synthesis of compounds with structures related to those present in some SERMs. All compounds 1, were prepared according to standard procedures.
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34
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(a) J. Barluenga, M. Marco-Arias, F. González-Bobes, A. Ballesteros and J. M. González, Chem. Eur. J., 2004, 10, 1677;
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For a recent review on stereoselective organic reactions in water, see: (a) U. M. Lindström, Chem. Rev., 2002, 102, 2751;
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For early work on intramolecular iodoarylation of alkynes, see: (a) J. Barluenga, J. M. González, P. J. Campos and G. Asensio, Angew. Chem., Int. Ed. Engl., 1988, 27, 1546;
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(b) for an elegant development en route to prepare fused polycyclic aromatic compounds, see: M. B. Goldfinger, K. B. Crawford and T. M. Swager, J. Am. Chem. Soc., 1997, 119, 4578.
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40
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18044394460
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note
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2 (15 mL/1 mmol of alkyne) 2k was obtained in 30% isolated yield.
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42
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0030994475
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(b) N. Hénaff, S. K. Stewart and A. Whiting, Tetrahedron Lett., 1997, 38, 4525.
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