Phenyl tributylstannyl selenide as a promising reagent for introducion of the phenylseleno group

Journal of Organic Chemistry

Volumn 68, Issue 9, 2003, Pages 3599-3602

  Nishiyama, Yutaka ^a   Kawamatsu, Hiroaki ^a   Funato, Saori ^a   Tokunaga, Keiji ^a   Sonoda, Noboru ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

REAGENTS;

CATALYSTS; ESTERS; PALLADIUM; SYNTHESIS (CHEMICAL);

SELENIUM COMPOUNDS;

CARBONYL DERIVATIVE; CHLORIDE; ESTER; ORGANOSELENIUM DERIVATIVE; PALLADIUM COMPLEX; PHENYL TRIBUTYLSTANNYL SELENIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; SYNTHESIS; TECHNIQUE;

EID: 0037414568     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026894i     Document Type: Article

References (85)

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5. Krief, A.; Hevesi, L. In Organoselenium Chemistry; Springer-Verlag: Berlin, 1988; Vol. 1. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: New York, 1986; Vols. 1 and 2. Krief, A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 85-192 and references therein.
6. Krief, A.; Hevesi, L. In Organoselenium Chemistry; Springer-Verlag: Berlin, 1988; Vol. 1. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: New York, 1986; Vols. 1 and 2. Krief, A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 85-192 and references therein.
7. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
8. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
9. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
10. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
11. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
12. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
13. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
14. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
15. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
16. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
17. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
18. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
19. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
20. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
21. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
22. There are some reports on the palladium complex catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Sato, T.; Nagai, Y. Angew. Chem. 1978, 17, 279. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715. Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895. Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748. Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3487. S-Sn: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683. Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
23. (a) Nishiyama, Y.; Tokunaga, K.; Sonoda, N. Org. Lett. 1999, 1, 1725.
24. (b) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. J. Organomet. Chem. 2000, 605, 96.
25. (c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Russ. J. Org. Chem. 2001, 37, 1463.
26. (a) Nishiyama, Y.; Aoyama, S.; Hamanaka, S. Phosphorus, Silicon, Sulfur 1993, 65, 1245.
27. (b) Nishiyama, Y.; Ohashi, H.; Itoh, K.; Sonoda, N. Chem. Lett. 1998, 159.
28. (c) Nishiyama, Y.; Tokunaga, K.; Kawamatsu, H.; Sonoda, N. Tetrahedron Lett. 2002, 1507.
29. Beletskaya has recently reported the utilization of phenyl tributylstannyl selenide, which was generated in situ by the reaction of diphenyl diselenide with hexabutyl distannane with daylight in organic synthesis. See: (a) Bumagin, N. A.; Gulevich, Y. V.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1984, 953. (b) Bumagin, N. A.; Gulevich, Y. V.; Beletskaya, I. P. J. Organomet. Chem. 1985, 285, 415. (c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Mendeleev Commun. 2000, 127.
30. Beletskaya has recently reported the utilization of phenyl tributylstannyl selenide, which was generated in situ by the reaction of diphenyl diselenide with hexabutyl distannane with daylight in organic synthesis. See: (a) Bumagin, N. A.; Gulevich, Y. V.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1984, 953. (b) Bumagin, N. A.; Gulevich, Y. V.; Beletskaya, I. P. J. Organomet. Chem. 1985, 285, 415. (c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Mendeleev Commun. 2000, 127.
31. Beletskaya has recently reported the utilization of phenyl tributylstannyl selenide, which was generated in situ by the reaction of diphenyl diselenide with hexabutyl distannane with daylight in organic synthesis. See: (a) Bumagin, N. A.; Gulevich, Y. V.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1984, 953. (b) Bumagin, N. A.; Gulevich, Y. V.; Beletskaya, I. P. J. Organomet. Chem. 1985, 285, 415. (c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Mendeleev Commun. 2000, 127.
32. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
33. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
34. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
35. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
36. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
37. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
38. The other applications of organoselenium compounds having a Se-Sn bond are very few due to the lack of method for the activation of the selenium-tin bond. See: (a) Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. (b) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. (c) Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. (d) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. (e) Stelius, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. (f) Baudler, H.; Suchomel, G.; Fuerstenberg, G.; Schings, O. Angew. Chem. 1981, 93, 1087. (g) Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
39. 0 = 98.2±3 Kcal/mol. See: Ho, K.C.M. In Thermodynamics Data for Inorganic Sulfides, Selenides, and Telurides; Rechhood Press: England, 1974; p 594.
40. (a) Bates, G.S.; Diakur, J.; Masamune, S. Tetrahedron Lett. 1976, 49, 4423.
41. (b) Grieco, P. A.; Yokoyama, Y.; Williams, E. J. Org. Chem. 1978, 43, 1283.
42. (c) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811 and references cited therein.
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44. For recent reviews on selenol esters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 461-484. (b) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katrizky, A. R., Meth-Cohn, O., Ress, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 5, pp 231-255.
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52. 16
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60. 3, which was synthesized by our method (see the Experimental Section), and benzoyl chloride under the similar reaction conditions to that of Beletskaya's report; however, the yield of Se-phenyl selenobenzoate (7) was low (24%).
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62. Rossi has reported the synthesis of -1-alkenyl phenylsulfides by the palladium-catalyzed reaction of 1-alkenyl bromides with tri-alkylstannyl phenylsulfide. In this paper, they proposed that the first step of this reaction was the generation of vinylpalladium bromide species by the reaction of 1-alkenyl bromides with low-valent palladium species. See: Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699.
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68. (f) Piettre, S.; Janousek, Z.; Viehe, H. G. Synthesis 1982, 1083.
69. (g) Denis, J. N.; Krief, A. J. Chem. Soc., Chem. Commun. 1983, 229.
70. (h) Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949.
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72. (j) Eaton, P. E.; Bunnelle, W. H. Tetrahedron Lett. 1984, 25, 23.
73. (k) Lerouge, P.; Paulmier, C. Tetrahedron Lett. 1984, 25, 1987.
74. See for examples: (a) Toru, T.; Watanabe, Y.; Yoneda, Y.; Ueno, Y. Tetrahedron Lett. 1990, 31, 6669.
75. (b) Toru, T.; Watanabe, Y.; Yoneda, T.; Okumura, T.; Ueno, Y. Bull. Chem. Soc. Jpn. 1993, 66, 3030 including references therein.
76. (a) Back, T.; Kerr, R. Tetrahedron Lett. 1982, 23, 3241.
77. (b) Sonoda, N.; Miyoshi, N.; Yamamoto, T.; Kambe, N.; Murai, S. Tetrahedron Lett. 1982, 23, 4813.
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81. 25
82. Simpson, J. H.; J. K. Stille, J. Org. Chem. 1985, 50, 1759.
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