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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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For the papers of transition-metal-catalyzed coupling of norbornenes with carbon nucleophiles and organoelectrophiles, see: Catallani, M.; Chiusoli, G. P. Tetrahedron Lett 1982, 23, 4517. Catallani, M.; Chiusoli, G. P.; Mari, A. J. Organomet. Chem. 1984, 275, 129. Catallani, M.; Chiusoli, G. P.; Concari, S. Tetrahedron 1989, 45, 5263. Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. Kosugi, M.; Taraura, H.; Sano, H.; Migita, T. Tetrahedron 1989, 45, 961. Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522. Oda, H.; Kobayashi, T.; Kosugi, M.; Migita, T. Tetrahedron 1995, 51, 695. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319. Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499. Torii, S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett. 1992, 33, 3503.
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Recently we reported the Ni-catalyzed tandem coupling of allyl chlorides, alkynes, and alkynyltins to yield 1-alkynyl-1,4-pentadienes. See: (a) Ikeda, S.; Cui, D.-M.; Sato, Y. J. Org. Chem. 1994, 59, 6877. Kosugi et al. reported that allyl bromide added to terminal alkynes in the presence of Pd catalyst to give 1-bromo-1,4-pentadienes which could further react with organotins to give 1-substituted 1,4-pentadiene. See: (b) Kosugi, M.; Sakaya, T.; Ogawa, S.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3058 and references cited therein.
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Recently we reported the Ni-catalyzed tandem coupling of allyl chlorides, alkynes, and alkynyltins to yield 1-alkynyl-1,4-pentadienes. See: (a) Ikeda, S.; Cui, D.-M.; Sato, Y. J. Org. Chem. 1994, 59, 6877. Kosugi et al. reported that allyl bromide added to terminal alkynes in the presence of Pd catalyst to give 1-bromo-1,4-pentadienes which could further react with organotins to give 1-substituted 1,4-pentadiene. See: (b) Kosugi, M.; Sakaya, T.; Ogawa, S.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3058 and references cited therein.
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3SiCl in the absence of 1a gave 5c (7c, 26% yield based on 1a after hydrolysis), along with a trace amount of 1b.
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3-(siloxy)allyl nickel complexes such as 10 were generated in situ and used without purification (contaminated with COD) in the stoichiometric reaction with halocarbon. See ref 9.
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