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For representative reviews, see: B. M. Trost, Tetrahedron, 1977, 33, 2615; J. Tsuji, Topics Curr. Chem. 1980, 91, 29; M. Kumada, Pure Appl. Chem. 1980, 52, 669; E. I. Negishi, Acc. Chem. Res. 1982, 75, 340; J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980; J. E. Bäckvall, Pure Appl. Chem. 1983, 55, 1669; R. H. Heck, Palladium Reagents for Organic Synthesis, Academic Press, New York, 1985; W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38; B. M. Trost, Acc. Chem. Res. 1990, 23, 34; R. C. Larock, Adv. Met.-Org. Chem. 1994, 3, 97; J. Tsuji, Transition Metal Reagents and Catalysis. Innovations in Organic Synthesis, Wiley-VCH, New York, 2000; G. Poli, G. Giambastiani, A. Heumann, Tetrahedon 2000, 56, 5959.
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For representative reviews, see: B. M. Trost, Tetrahedron, 1977, 33, 2615; J. Tsuji, Topics Curr. Chem. 1980, 91, 29; M. Kumada, Pure Appl. Chem. 1980, 52, 669; E. I. Negishi, Acc. Chem. Res. 1982, 75, 340; J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980; J. E. Bäckvall, Pure Appl. Chem. 1983, 55, 1669; R. H. Heck, Palladium Reagents for Organic Synthesis, Academic Press, New York, 1985; W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38; B. M. Trost, Acc. Chem. Res. 1990, 23, 34; R. C. Larock, Adv. Met.-Org. Chem. 1994, 3, 97; J. Tsuji, Transition Metal Reagents and Catalysis. Innovations in Organic Synthesis, Wiley-VCH, New York, 2000; G. Poli, G. Giambastiani, A. Heumann, Tetrahedon 2000, 56, 5959.
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For representative reviews, see: B. M. Trost, Tetrahedron, 1977, 33, 2615; J. Tsuji, Topics Curr. Chem. 1980, 91, 29; M. Kumada, Pure Appl. Chem. 1980, 52, 669; E. I. Negishi, Acc. Chem. Res. 1982, 75, 340; J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980; J. E. Bäckvall, Pure Appl. Chem. 1983, 55, 1669; R. H. Heck, Palladium Reagents for Organic Synthesis, Academic Press, New York, 1985; W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38; B. M. Trost, Acc. Chem. Res. 1990, 23, 34; R. C. Larock, Adv. Met.-Org. Chem. 1994, 3, 97; J. Tsuji, Transition Metal Reagents and Catalysis. Innovations in Organic Synthesis, Wiley-VCH, New York, 2000; G. Poli, G. Giambastiani, A. Heumann, Tetrahedon 2000, 56, 5959.
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For representative reviews, see: B. M. Trost, Tetrahedron, 1977, 33, 2615; J. Tsuji, Topics Curr. Chem. 1980, 91, 29; M. Kumada, Pure Appl. Chem. 1980, 52, 669; E. I. Negishi, Acc. Chem. Res. 1982, 75, 340; J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980; J. E. Bäckvall, Pure Appl. Chem. 1983, 55, 1669; R. H. Heck, Palladium Reagents for Organic Synthesis, Academic Press, New York, 1985; W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38; B. M. Trost, Acc. Chem. Res. 1990, 23, 34; R. C. Larock, Adv. Met.-Org. Chem. 1994, 3, 97; J. Tsuji, Transition Metal Reagents and Catalysis. Innovations in Organic Synthesis, Wiley-VCH, New York, 2000; G. Poli, G. Giambastiani, A. Heumann, Tetrahedon 2000, 56, 5959.
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For representative reviews on transition metal-catalyzed reactions in aqueous media, see: F. Joo, Z. Toth, J. Mol. Catal. 1980, 8, 369; D. Sinou, Bull. Soc. Chim. Fr. 1987, 480; E. G. Kuntz, Chemtech 1987, 17, 570; P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219; W. A. Herrmann, C. W. Kolpaintner, Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
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For representative reviews on transition metal-catalyzed reactions in aqueous media, see: F. Joo, Z. Toth, J. Mol. Catal. 1980, 8, 369; D. Sinou, Bull. Soc. Chim. Fr. 1987, 480; E. G. Kuntz, Chemtech 1987, 17, 570; P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219; W. A. Herrmann, C. W. Kolpaintner, Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
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For representative reviews on transition metal-catalyzed reactions in aqueous media, see: F. Joo, Z. Toth, J. Mol. Catal. 1980, 8, 369; D. Sinou, Bull. Soc. Chim. Fr. 1987, 480; E. G. Kuntz, Chemtech 1987, 17, 570; P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219; W. A. Herrmann, C. W. Kolpaintner, Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
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For representative reviews on transition metal-catalyzed reactions in aqueous media, see: F. Joo, Z. Toth, J. Mol. Catal. 1980, 8, 369; D. Sinou, Bull. Soc. Chim. Fr. 1987, 480; E. G. Kuntz, Chemtech 1987, 17, 570; P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219; W. A. Herrmann, C. W. Kolpaintner, Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
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Previously, Pd/C was used as the catalyst for Ullmann-type coupling with moderate yields under phase-transfer conditions by refluxing at 100°C, see: P. Bamfield, P. M. Quan, Synthesis 1978, 537.
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No reaction was observed with Fe. The use of Mn powder produced a GC/MS ratio of 76:26 (coupling: dehalogenation) under the same reaction conditions.
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55
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0348204456
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note
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No significant benefit was observed with β-cyclodextrin or benzil as the chelating agents.
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