Palladium-catalyzed cross-coupling reaction of triarylbismuths with aryl halides and triflates

Organic Letters

Volumn 3, Issue 25, 2001, Pages 4103-4105

  Rao, Maddali L N ^a   Yamazaki, Osamu ^a   Shimada, Shigeru ^a   Tanaka, Toshifumi ^b   Suzuki, Yohichi ^b   Tanaka, Masato ^a,b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b NIHON UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000136859     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016885g     Document Type: Article

References (18)

1. Metal-Catalyzed, Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
2. Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic & Professional: London, 1998; Chapter 6. Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683.
3. Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic & Professional: London, 1998; Chapter 6. Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683.
4. Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic & Professional: London, 1998; Chapter 6. Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683.
5. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
6. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
7. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
8. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
9. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
10. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
11. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
12. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
13. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
14. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
15. Examples of Pd complex-mediated or -catalyzed reaction of organobismuth compounds: Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661. Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425. Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. Cho, C. S.; Yoshimori, Y.; Uemura, S. Bull. Chem. Soc. Jpn. 1995, 68, 950. Huang, X.; Wu, J. L. Chin. Chem. Lett. 1997, 8, 759. Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1999, 72, 1851. Kang, S. K.; Ryu, H. C.; Kim, J. W. Synth. Commun. 2001, 31, 1021. Kang, S. K.; Ryu, H. C.; Lee, S. W. Synth. Commun. 2001, 31, 1027. Kang, S. K.; Ryu, H. C.; Hong, Y. T.; Kim, M. S.; Lee, S. W.; Jung, J. H. Synth. Commun. 2001, 31, 2365.
16. Rao, M. L. N.; Shimada, S.; Tanaka, M. Org. Lett. 1999, 1, 1271.
17. Shimada, S.; Rao, M. L. N.; Tanaka, M. Organometallics 2000, 19, 931.
18. 4, filtered, and concentrated in vacuo. The residue was purified by preparative TLC to give 64 mg (86%) of 4-acetylbiphenyl.