Propargylic dithioacetal as an allene 1,3-dication synthon. Nickel-catalyzed cross-coupling reactions of propargylic dithioacetals with Grignard reagents

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8685-8686

  Tseng, Hsian Rong ^a   Luh, Tien Yau ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000559068     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961514c     Document Type: Article

References (31)

1. For reviews, see: (a) Tsuji, J.; Mandai, T. J. Organomet. Chem. 1993, 451, 15. (b) Tsuji, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (c) Tsuji, J.; Mandai, T. Synthesis 1996, 1. (d) Landor, S. R., Ed. The Chemistry of Allenes; Academic Press: London, 1982.
2. For reviews, see: (a) Tsuji, J.; Mandai, T. J. Organomet. Chem. 1993, 451, 15. (b) Tsuji, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (c) Tsuji, J.; Mandai, T. Synthesis 1996, 1. (d) Landor, S. R., Ed. The Chemistry of Allenes; Academic Press: London, 1982.
3. For reviews, see: (a) Tsuji, J.; Mandai, T. J. Organomet. Chem. 1993, 451, 15. (b) Tsuji, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (c) Tsuji, J.; Mandai, T. Synthesis 1996, 1. (d) Landor, S. R., Ed. The Chemistry of Allenes; Academic Press: London, 1982.
4. For reviews, see: (a) Tsuji, J.; Mandai, T. J. Organomet. Chem. 1993, 451, 15. (b) Tsuji, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (c) Tsuji, J.; Mandai, T. Synthesis 1996, 1. (d) Landor, S. R., Ed. The Chemistry of Allenes; Academic Press: London, 1982.
5. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
6. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
7. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
8. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
9. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
10. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
11. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
12. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
13. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
14. For recent syntheses, see: (a) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. J. Org. Chem. 1995, 60, 863. (b) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organomet. Chem. 1995, 9, 369. (c) Hojo, F.; Ando, W. Synlett 1995, 880. (d) Kirms, M. A.; Salcido, S. L.; Kirms, L. M. Tetrahedron Lett. 1995, 36, 7979. (e) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925. (f) Holmann, M.; Krause, M. Chem. Ber. 1995, 128, 851. (g) Besson, L.; Gore, J.; Gazes, B. Tetrahedron Lett. 1995, 36, 3853. (h) Yamamoto, Y.; Almasum, M.; Asao, N. J. Am. Chem. Soc. 1995, 117, 2379. (i) Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K. J. Org. Chem. 1995, 60, 4650. (j) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
15. For reviews, see: (a) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (b) Luh T.-Y.; Ni, Z.-J. Synthesis 1990, 89. (c) Luh T.-Y.; Leung, M.-K. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI: London, 1996; Vol. 2, p 109. (d) Luh, T.-Y. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992; p 229. (e) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 105. (f) Luh, T.-Y. Synlett 1996, 201.
16. For reviews, see: (a) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (b) Luh T.-Y.; Ni, Z.-J. Synthesis 1990, 89. (c) Luh T.-Y.; Leung, M.-K. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI: London, 1996; Vol. 2, p 109. (d) Luh, T.-Y. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992; p 229. (e) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 105. (f) Luh, T.-Y. Synlett 1996, 201.
17. For reviews, see: (a) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (b) Luh T.-Y.; Ni, Z.-J. Synthesis 1990, 89. (c) Luh T.-Y.; Leung, M.-K. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI: London, 1996; Vol. 2, p 109. (d) Luh, T.-Y. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992; p 229. (e) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 105. (f) Luh, T.-Y. Synlett 1996, 201.
18. For reviews, see: (a) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (b) Luh T.-Y.; Ni, Z.-J. Synthesis 1990, 89. (c) Luh T.-Y.; Leung, M.-K. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI: London, 1996; Vol. 2, p 109. (d) Luh, T.-Y. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992; p 229. (e) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 105. (f) Luh, T.-Y. Synlett 1996, 201.
19. For reviews, see: (a) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (b) Luh T.-Y.; Ni, Z.-J. Synthesis 1990, 89. (c) Luh T.-Y.; Leung, M.-K. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI: London, 1996; Vol. 2, p 109. (d) Luh, T.-Y. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992; p 229. (e) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 105. (f) Luh, T.-Y. Synlett 1996, 201.
20. For reviews, see: (a) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (b) Luh T.-Y.; Ni, Z.-J. Synthesis 1990, 89. (c) Luh T.-Y.; Leung, M.-K. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI: London, 1996; Vol. 2, p 109. (d) Luh, T.-Y. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992; p 229. (e) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 105. (f) Luh, T.-Y. Synlett 1996, 201.
21. (a) Ni, Z.-J.; Mei, N.-W.; Shi, X.; Wang, M. C.; Tzeng Y.-L.; Luh, T.-Y. J. Org. Chem. 1991, 56, 4035 and references therein.
22. (b) Shiu, L.-L.; Yu, C. C.; Wong, K.-T.; Chen, B.-L.; Cheng, W.-L.; Yuan, T.-M.; Luh, T.-Y.Oragnometallics 1993, 12, 1018.
23. (c) Wong, K.-T.; Yuan, T.-M.; Wang, M. C.; Tung, H.-H.; Luh, T.-Y. J. Am. Chem. Soc. 1994, 116, 8920 and references therein.
24. (d) Cheng W.-L.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1992, 1392.
25. (a) Tzeng, Y.-L.; Yang, P.-F.; Mei, N.-W.; Yuan, T.-M.; Yu C. C.; Luh, T.-Y. J. Org. Chem. 1991, 56, 5289.
26. (b) Yuan, T.-M.; Luh, T.-Y. J. Org. Chem. 1991, 57, 4550.
27. Methanol solvent is essential for this transformation. (Cf. Williams, J. R.; Sarkisian, G. M. Synthesis 1974, 32. Yuan, T.-M.; Luh, T.-Y. Org. Synth. 1996, 74, in press).
28. Methanol solvent is essential for this transformation. (Cf. Williams, J. R.; Sarkisian, G. M. Synthesis 1974, 32. Yuan, T.-M.; Luh, T.-Y. Org. Synth. 1996, 74, in press).
29. Aral, K.; Iwamura, H.; Oki, M. Bull. Chem. Jpn. 1975, 48, 3319.
30. Jacobs, T. L.; Prempree, P. J. Am. Chem. Soc. 1967, 89, 6177.
31. Ziegler, K.; Sauermilch, W. Ber. 1930, 63, 1851.