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The syntheses of biaryls by palladium-catalyzed couplings of aryl halides with other arene derivatives are well established processes, e.g. with boronic acids (Suzuki protocol [3a]), with stannanes (Stille protocol) [3b], see also: R.T. Kelly, I. Tellitu, J.P. Sestelo, Angew. Chem. 109 (1997) 1969; Angew. Chem. Int. Ed. Engl. 36 (1997) 1866. With silanes see: Y. Hatanaka, K.-i. Goda, Y. Okahara, T. Hiyama, Tetrahedron 50 (1994) 8301. Or with the corresponding arenes themselves intramolecular: T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 109 (1997) 1820; Angew. Chem. Int. Ed. Engl. 36 (1997) 1740.
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The syntheses of biaryls by palladium-catalyzed couplings of aryl halides with other arene derivatives are well established processes, e.g. with boronic acids (Suzuki protocol [3a]), with stannanes (Stille protocol) [3b], see also: R.T. Kelly, I. Tellitu, J.P. Sestelo, Angew. Chem. 109 (1997) 1969; Angew. Chem. Int. Ed. Engl. 36 (1997) 1866. With silanes see: Y. Hatanaka, K.-i. Goda, Y. Okahara, T. Hiyama, Tetrahedron 50 (1994) 8301. Or with the corresponding arenes themselves intramolecular: T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 109 (1997) 1820; Angew. Chem. Int. Ed. Engl. 36 (1997) 1740.
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The syntheses of biaryls by palladium-catalyzed couplings of aryl halides with other arene derivatives are well established processes, e.g. with boronic acids (Suzuki protocol [3a]), with stannanes (Stille protocol) [3b], see also: R.T. Kelly, I. Tellitu, J.P. Sestelo, Angew. Chem. 109 (1997) 1969; Angew. Chem. Int. Ed. Engl. 36 (1997) 1866. With silanes see: Y. Hatanaka, K.-i. Goda, Y. Okahara, T. Hiyama, Tetrahedron 50 (1994) 8301. Or with the corresponding arenes themselves intramolecular: T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 109 (1997) 1820; Angew. Chem. Int. Ed. Engl. 36 (1997) 1740.
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The syntheses of biaryls by palladium-catalyzed couplings of aryl halides with other arene derivatives are well established processes, e.g. with boronic acids (Suzuki protocol [3a]), with stannanes (Stille protocol) [3b], see also: R.T. Kelly, I. Tellitu, J.P. Sestelo, Angew. Chem. 109 (1997) 1969; Angew. Chem. Int. Ed. Engl. 36 (1997) 1866. With silanes see: Y. Hatanaka, K.-i. Goda, Y. Okahara, T. Hiyama, Tetrahedron 50 (1994) 8301. Or with the corresponding arenes themselves intramolecular: T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 109 (1997) 1820; Angew. Chem. Int. Ed. Engl. 36 (1997) 1740.
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This type of reaction has previously been regarded as involving ortho-C-H activation, but the term 'Friedel Crafts type' alkylation might be more appropriate in view of the probable mechanism of this process: D. Brown, R. Grigg, V. Sridharan, V. Tambyrah, Tetrahedron Lett. 36 (1995) 8137.
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Propargyl carbonates have been shown to react with methyl acrylate under palladium catalysis to give ethenylallenes. Cf. T. Mandai, M. Ogawa, H. Yamaoki, T. Nakata, H. Murayama, M. Kawada, J. Tsuji, Tetrahedron Lett. 32 (1991) 3397.
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0347375523
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note
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As has previously been proved, most or all putative 6- and 1-endo-trig carbopalladations proceeded by a sequence of (n-1)-exo-trig, 3-exo-trig cyclization and subsequent ring-enlarging cyclopropylcarbinyl to homoallyl rearrangement. Cf. E. Negishi et al. [13b].
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0347375513
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note
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The substitution reaction on complexes of type 279 proceeds with retention of the cyclopropyl group: S. Bräse, J.E. Bäckvall, A. de Meijere (unpublished results).
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