1,6-Diene complexes of palladium(0) and platinum(0): Highly reactive sources for the naked metals and [L-M0] fragments

Journal of the American Chemical Society

Volumn 121, Issue 42, 1999, Pages 9807-9823

  Krause, Jochen ^a   Cestaric, Günter ^a   Haack, Karl Josef ^a   Seevogel, Klaus ^a   Storm, Werner ^a   Pörschke, Klaus Richard ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX; PLATINUM COMPLEX;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033610479     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983939h     Document Type: Article

References (140)

1. For reviews of representative reactions, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Hermann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann W. A., Eds.; Weinheim: VCH, 1996; Vol. 2, p 712. (c) Friesen, R. W. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 7, p 4788.
2. For reviews of representative reactions, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Hermann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann W. A., Eds.; Weinheim: VCH, 1996; Vol. 2, p 712. (c) Friesen, R. W. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 7, p 4788.
3. For reviews of representative reactions, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Hermann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann W. A., Eds.; Weinheim: VCH, 1996; Vol. 2, p 712. (c) Friesen, R. W. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 7, p 4788.
4. For reviews of representative reactions, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Hermann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann W. A., Eds.; Weinheim: VCH, 1996; Vol. 2, p 712. (c) Friesen, R. W. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 7, p 4788.
5. (a) Stille, J. R. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 1, p 482.
6. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. 1995, 107, 1456; Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
7. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. 1995, 107, 1456; Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
8. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. 1995, 107, 1456; Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
9. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
10. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
11. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
12. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
13. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
14. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
15. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
16. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
17. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
18. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
19. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
20. 4 as catalyt: (a) Di- and Silaboration of Alkenes and Alkynes. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713. Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777. Ishiyama, T.; Yamamoto, M.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1997, 689, 2073. (b) Hydrosilylation of Alkenes and Alkynes. Marciniec, B.; Gulinski, J.; Urbaniak, W.; Nowicka, T.; Mirecki, J. Appl. Organomet. Chem. 1990, 4, 27. Itoh, M.; Iwata, K.; Takeuchi, R.; Kobayashi, M. J. Organomet. Chem. 1991, 420, C5. Gevorgyan, V.; Borisova, L.; Popelis, J.; Lukevics, E.; Foltynowicz, Z.; Gulinski, J.; Marciniec, B. J. Organomet. Chem. 1992, 424, 15. Kusumoto, T.; Ando, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 1992, 65, 1280. (c) Hydrosulfuration and -selenation of Alkynes. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380. (d) Thiosilylation of Alkynes. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 8249.
21. (a) Malatesta, L.; Angoletta, M. J. Chem. Soc. (London) 1957, 1186.
22. (b) Fischer, E. O.; Werner, H. Chem. Ber. 1962, 95, 703.
23. (c) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
24. (a) Kuran, W.; Musco, A. J. Organomet. Chem. 1972, 40, C47.
25. (b) Kuran, W.; Musco, A. Inorg. Chim. Acta 1975, 12, 187. Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
26. (b) Kuran, W.; Musco, A. Inorg. Chim. Acta 1975, 12, 187. Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
27. Urata, H.; Suzuki, H.; Moro-oka, Y.; Ikawa, T. J. Organomet. Chem. 1989, 364, 235.
28. 3P)Pd] [Registry number supplied by author: 12628-74-9] intermediate, see: Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890. Grushin, V. V.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3259.
29. 3P)Pd] [Registry number supplied by author: 12628-74-9] intermediate, see: Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890. Grushin, V. V.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3259.
30. (a) Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc., Chem. Commun. 1970, 1065. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
31. (a) Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc., Chem. Commun. 1970, 1065. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
32. (b) Mazza, M. C.; Pierpont, C. G. Inorg. Chem. 1973, 12, 2955 and 1974, 13, 1891.
33. (b) Mazza, M. C.; Pierpont, C. G. Inorg. Chem. 1973, 12, 2955 and 1974, 13, 1891.
34. Herrmann, W. A.; Thiel, W. R.; Brossmer, C.; Öfele, K.; Priermeier, T.; Scherer, W. J. Organomet. Chem. 1993, 461, 51.
35. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373. Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
36. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373. Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
37. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373. Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
38. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373. Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
39. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373. Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
40. Döhring, A.; Jolly, P. W.; Mynott, R.; Schick, K.-P.; Wilke, G. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1981, 36, 1198. Jolly, P. W. Angew. Chem. 1985, 97, 279; Angew. Chem., Int. Ed. Engl. 1985, 24, 283.
41. Döhring, A.; Jolly, P. W.; Mynott, R.; Schick, K.-P.; Wilke, G. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1981, 36, 1198. Jolly, P. W. Angew. Chem. 1985, 97, 279; Angew. Chem., Int. Ed. Engl. 1985, 24, 283.
42. Döhring, A.; Jolly, P. W.; Mynott, R.; Schick, K.-P.; Wilke, G. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1981, 36, 1198. Jolly, P. W. Angew. Chem. 1985, 97, 279; Angew. Chem., Int. Ed. Engl. 1985, 24, 283.
43. (a) Stannole synthesis: Krause, J.; Pluta, C.; Pörschke, K.-R.; Goddard, R. J. Chem. Soc., Chem. Commun. 1993, 1254. Krause, J.; Haack, K.-J.; Pörschke, K.-R.; Gabor, B.; Goddard, R.; Pluta, C.; Seevogel, K. J. Am. Chem. Soc. 1996, 118, 804.
44. (a) Stannole synthesis: Krause, J.; Pluta, C.; Pörschke, K.-R.; Goddard, R. J. Chem. Soc., Chem. Commun. 1993, 1254. Krause, J.; Haack, K.-J.; Pörschke, K.-R.; Gabor, B.; Goddard, R.; Pluta, C.; Seevogel, K. J. Am. Chem. Soc. 1996, 118, 804.
45. (b) Linear trimerization of alk-1-ynes: see ref 52.
46. (a) Krause, J. Dissertation, Universität Düsseldorf, 1993.
47. (b) Haack, K.-J. Dissertation, Universität Dusseldorf, 1994.
48. (c) Cestaric, G. Dissertation, Universität Düsseldorf, 1999.
49. (a) Green, M.; Howard, J. A. K.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1975, 449.
50. (b) Green, M.; Howard, J. A. K.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1977, 271.
51. (c) Stone, F. G. A. Acc. Chem. Res. 1981, 14, 318.
52. (a) Yamamoto, T.; Ishizu, J.; Yamamoto, A. Chem. Lett. 1979, 1385. Yamamoto, T.; Ishizu, J.; Yamamoto. A. J. Am. Chem. Soc. 1981, 103, 6863.
53. (a) Yamamoto, T.; Ishizu, J.; Yamamoto, A. Chem. Lett. 1979, 1385. Yamamoto, T.; Ishizu, J.; Yamamoto. A. J. Am. Chem. Soc. 1981, 103, 6863.
54. (b) Yamamoto, T.; Akimoto, M.; Yamamoto, A. Chem. Lett. 1983, 1725. Yamamoto, T.; Akimoto, M.; Saito, O.; Yamamoto, A. Organometallics 1986, 5, 1559.
55. (b) Yamamoto, T.; Akimoto, M.; Yamamoto, A. Chem. Lett. 1983, 1725. Yamamoto, T.; Akimoto, M.; Saito, O.; Yamamoto, A. Organometallics 1986, 5, 1559.
56. (a) Proft, B.; Pörschke, K.-R.; Lutz, F.; Krüger, C. Chem. Ber. 1991, 124, 2667.
57. (b) Pluta, C.; Pörschke, K.-R.; Gabor, B.; Mynott, R. Chem. Ber. 1994, 127, 489. Rosenthal, U.; Pulst, S.; Kempe, R.; Pörschke, K.-R.; Goddard, R.; Proft, B. Tetrahedron 1998, 54, 1277.
58. (b) Pluta, C.; Pörschke, K.-R.; Gabor, B.; Mynott, R. Chem. Ber. 1994, 127, 489. Rosenthal, U.; Pulst, S.; Kempe, R.; Pörschke, K.-R.; Goddard, R.; Proft, B. Tetrahedron 1998, 54, 1277.
59. (c) Proft, B. Dissertation, Universität Düsseldorf, 1993.
60. (d) Trebbe, R. Planned Dissertation.
61. Krause, J.; Haack, K.-J.; Cestaric, G.; Goddard, R.; Pörschke, K.-R. J. Chem. Soc., Chem. Commun. 1998, 1291.
62. (a) Hitchcock, P. B.; Lappert, M. F.; Warhurst, N. J. W. Angew. Chem. 1991, 103, 439; Angew. Chem., Int. Ed. Engl. 1991, 30, 438.
63. (a) Hitchcock, P. B.; Lappert, M. F.; Warhurst, N. J. W. Angew. Chem. 1991, 103, 439; Angew. Chem., Int. Ed. Engl. 1991, 30, 438.
64. (b) Beuter, G.; Heyke, O.; Lorenz, I.-P. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1991, 46, 1694.
65. (c) Chandra, G.; Lo, P. Y. K. European Patent Application EP 182611, May 28, 1986; Chem. Abstr. 1986, 105, 153341y. Chandra, G.; Lo, P. Y.; Hitchcock, P. B.; Lappert, M. F. Organometallics 1987, 6, 191.
66. (c) Chandra, G.; Lo, P. Y. K. European Patent Application EP 182611, May 28, 1986; Chem. Abstr. 1986, 105, 153341y. Chandra, G.; Lo, P. Y.; Hitchcock, P. B.; Lappert, M. F. Organometallics 1987, 6, 191.
67. (d) Bassindale, A. R.; Brown, S. S. D.; Lo, P. Organometallics 1994, 13, 738. Avent, A. G.; Lappert, M. F.; MacBeath, C. J. Organomet. Chem. 1995, 502, 163.
68. (d) Bassindale, A. R.; Brown, S. S. D.; Lo, P. Organometallics 1994, 13, 738. Avent, A. G.; Lappert, M. F.; MacBeath, C. J. Organomet. Chem. 1995, 502, 163.
69. Bogdanovic, B.; Kröner, M.; Wilke, G. Liebigs Ann. Chem. 1966, 699, 1.
70. (a) Müller, J.; Göser, P. Angew. Chem. 1967, 79, 380; Angew. Chem., Int. Ed. Engl. 1967, 6, 364.
71. (a) Müller, J.; Göser, P. Angew. Chem. 1967, 79, 380; Angew. Chem., Int. Ed. Engl. 1967, 6, 364.
72. (b) Herberich, G. E.; Hessner, B. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1979, 34, 638.
73. 2 in neat hepta-1,6-diene results in deposition of elemental palladium, instead of the formation of 1.
74. 13C NMR spectrum (27°C).
75. Hitchcock, P. B.; Lappert, M. F.; MacBeath, C.; Scott, F. P. E.; Warhurst, N. J. W. J. Organomet. Chem. 1997, 528, 185.
76. Lappert, M. F.; Scott, F. P. A. J. Organomet. Chem. 1995, 492, C11.
77. s symmetrical, chairlike conformation in the ground state.
78. (b) Paiaro, G. Organomet. Chem. Rev., Sect. A 1970, 6, 319.
79. 26b The coordination of the ethene ligand in these complexes is static as compared to the NMR time scale. (a) Krause, J.; Bonrath, W.; Pörschke, K.-R. Organometallics 1992, 11, 1158. (b) Schager, F.; Haack, K.-J.; Mynott, R.; Rufinska, A.; Pörschke, K.-R. Organometallics 1998, 17, 807.
80. 26b The coordination of the ethene ligand in these complexes is static as compared to the NMR time scale. (a) Krause, J.; Bonrath, W.; Pörschke, K.-R. Organometallics 1992, 11, 1158. (b) Schager, F.; Haack, K.-J.; Mynott, R.; Rufinska, A.; Pörschke, K.-R. Organometallics 1998, 17, 807.
81. 5N)Pd(dvds) have failed.
82. (a) Tolman, C. A. Chem. Rev. 1977, 77, 313.
83. 3P the given cone angle of 194° appears to be overestimated, and on the basis of chemical experience a value of about 170° reflects the steric bulk of this phosphane more reasonably.
84. (a) Matsumoto, M.; Yoshioka, H.; Nakatsu, K.; Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1974, 96, 3323. Otsuka, S ; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850. Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 101. Tanaka, M. Acta Crystallogr., Part C 1992, 48, 739.
85. (a) Matsumoto, M.; Yoshioka, H.; Nakatsu, K.; Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1974, 96, 3323. Otsuka, S ; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850. Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 101. Tanaka, M. Acta Crystallogr., Part C 1992, 48, 739.
86. (a) Matsumoto, M.; Yoshioka, H.; Nakatsu, K.; Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1974, 96, 3323. Otsuka, S ; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850. Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 101. Tanaka, M. Acta Crystallogr., Part C 1992, 48, 739.
87. (a) Matsumoto, M.; Yoshioka, H.; Nakatsu, K.; Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1974, 96, 3323. Otsuka, S ; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850. Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 101. Tanaka, M. Acta Crystallogr., Part C 1992, 48, 739.
88. 8 is temperature dependent: δ(P) 85.8 (27°C), 83.6 (-30°C), 82.0 (-80°C).
89. 3P/Pd catalyst systems, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617 and 2367. (b) Littke, A. F.; Fu, G. C. Angew. Chem. 1998, 110, 3586; Angew. Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Mann, G.; Incarvito, C ; Rheingold, A L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
90. 3P/Pd catalyst systems, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617 and 2367. (b) Littke, A. F.; Fu, G. C. Angew. Chem. 1998, 110, 3586; Angew. Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Mann, G.; Incarvito, C ; Rheingold, A L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
91. 3P/Pd catalyst systems, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617 and 2367. (b) Littke, A. F.; Fu, G. C. Angew. Chem. 1998, 110, 3586; Angew. Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Mann, G.; Incarvito, C ; Rheingold, A L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
92. 3P/Pd catalyst systems, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617 and 2367. (b) Littke, A. F.; Fu, G. C. Angew. Chem. 1998, 110, 3586; Angew. Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Mann, G.; Incarvito, C ; Rheingold, A L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
93. (a) Nakazawa, H.; Ozawa, F.; Yamamoto, A. Organometallics 1983, 2, 241.
94. (b) de Graaf, W.; Boersma, J.; Grove, D.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1988, 107, 299. de Graaf, W.; Boersma, J.; Smeets, W J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907.
95. (b) de Graaf, W.; Boersma, J.; Grove, D.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1988, 107, 299. de Graaf, W.; Boersma, J.; Smeets, W J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907.
96. (c) de Graaf, W.; Boersma, J.; van Koten, G. Organometallics 1990, 9, 1479.
97. 31P NMR (-30°C): δ 33.6.
98. 2 does not occur in the absence or in a dilluted hepta-1,6-diene solution, nor in neat hexa-1,5-diene, cod, or other dienes with a C=C bond sequence different from 1,6.
99. 3P)Pd(1,6-diene) complexes 25 and 35, respectively.
100. 2Pd (δ(P) 23.2) is obtained already at 20°C.
101. Tooze, R.; Chiu, K. W.; Wilkinson, G. Polyhedron 1984, 3, 1025.
102. (a) Werner, H. Angew. Chem. 1977, 89, 1; Angew. Chem., Int. Ed. Engl. 1977, 16, 1.
103. (a) Werner, H. Angew. Chem. 1977, 89, 1; Angew. Chem., Int. Ed. Engl. 1977, 16, 1.
104. (b) Werner, H.; Kuhn, A. Angew. Chem. 1977, 89, 427; Angew Chem., Int. Ed. Engl. 1977, 16, 412
105. (b) Werner, H.; Kuhn, A. Angew. Chem. 1977, 89, 427; Angew Chem., Int. Ed. Engl. 1977, 16, 412
106. Henc, B ; Jolly, P. W.; Salz, R.; Stobbe, S.; Wilke, G.; Benn, R.; Mynott, R.; Seevosel, K.; Goddard, R.; Krüger, C. J. Organomet. Chem. 1980, 191, 449.
107. (a) Werner, H. Adv. Organomet. Chem. 1981, 19, 155 and references therein.
108. (b) Jolly, P. W.; Kruger, C.; Schick, K.-P.; Wilke, G. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1980, 55, 926. Benn, R.; Jolly, P. W.; Mynott, R.; Raspel, B.; Schenker, G.; Schick, K.-P.; Schroth, G. Organometallics 1985, 4, 1945.
109. (b) Jolly, P. W.; Kruger, C.; Schick, K.-P.; Wilke, G. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1980, 55, 926. Benn, R.; Jolly, P. W.; Mynott, R.; Raspel, B.; Schenker, G.; Schick, K.-P.; Schroth, G. Organometallics 1985, 4, 1945.
110. (a) Büch, H. M. Dissertation (P. Binger), Universität Kaiserslautern (Germany), 1982, p 27.
111. 31P NMR: δ 47.3.
112. 3-allyl) complexes with isocyanides RNC, see: Otsuka, S.; Nakamura, A.; Tatsuno, Y. J. Am. Chem. Soc. 1969, 91, 6994 and ref 4b
113. 0] moiety seems to be very general.
114. ax- in M(dvds) complexes.
115. 2 symmetry).
116. free alkene. Thus, typical alkene coordination shifts to higher field are negative. Jolly, P. W.; Mynott, R. Adv. Organomet. Chem. 1981, 19, 257.
117. 18d
118. 18d
119. Nickel, T.; Pörschke, K.-R.; Goddard, R.; Krüger, C. Inorg. Chem. 1992, 31, 4428.
120. Pauling, L. Die Natur der Chemischen Bindung, 3rd ed.; VCH: Weinheim, Germany, 1976.
121. Dreher, E.; Gabor, B.; Jolly, P. W.; Kopiske, C.; Krüger, C.; Limberg, A.; Mynott, R. Organometallics 1995, 14, 1893.
122. 3P ligand with locked handedness.
123. 2-alkene) complex the charge withdrawal from phosphorus by the trans coordinated C=C group is larger than that in 16e TP-3 27 and 36 by two C=C groups.
124. (a) Krause, J.; Pörschke, K.-R. 5th International Conference on the Chemistry of the Platinum Group Metals, St. Andrews, U.K., July 11-16, 1993, A199.
125. (b) Krause, J.; Schager, F.; Pörschke, K.-R. 32nd International Conference on Coordination Chemistry (ICCC), Santiago, Chile, Aug 24-29, 1997, 7O4. Cestaric, G.; Krause, J.; Pörschke, K.-R. Manuscript in preparation.
126. (b) Krause, J.; Schager, F.; Pörschke, K.-R. 32nd International Conference on Coordination Chemistry (ICCC), Santiago, Chile, Aug 24-29, 1997, 7O4. Cestaric, G.; Krause, J.; Pörschke, K.-R. Manuscript in preparation.
127. Krause, J.; Pörschke, K.-R. To be submitted for publication.
128. Vollmüller, F.; Krause, J.; Klein, S.; Mägerlein, W.; Beller, M. Submitted.
129. (a) Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Mitchell, T. N. Synthesis 1992, 803.
130. (a) Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Mitchell, T. N. Synthesis 1992, 803.
131. (a) Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Mitchell, T. N. Synthesis 1992, 803.
132. (a) Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Mitchell, T. N. Synthesis 1992, 803.
133. 0] species as the "true catalyst". No second phosphane ligand is necessary to act in the catalytic cycle. Krause, J.; Pörschke, K.-R. Unpublished results.
134. Hartwig, J. F. Synlett 1998, 329.
135. Proft, B.; Pörschke, K.-R.; Lutz, F.; Krüger, C. Chem. Ber. 1994, 127, 653.
136. (a) Chatt, J.; Vallarino, L. M.; Venanzi, L. M. J. Chem. Soc. 1957, 3413.
137. (b) Chatt, J.; Vallarino, L. M.; Venanzi, L. M. J. Chem. Soc. 1957, 2496. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521.
138. (b) Chatt, J.; Vallarino, L. M.; Venanzi, L. M. J. Chem. Soc. 1957, 2496. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521.
139. (a) Shaw, B. L. Proc. Chem. Soc., London 1960, 247.
140. (b) Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 220.