Reactions of geminal dication synthons with geminal dianionic species. Cross coupling of benzylic dithioacetals with nickela-bimetallic reagents

Organometallics

Volumn 15, Issue 13, 1996, Pages 3099-3101

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

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001205238     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9601108     Document Type: Article

References (19)

1. For a recent review, see: Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, Chapter 3.4.
2. 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 129. (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.
3. 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 129. (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.
4. 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 129. (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.
5. 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 129. (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.
6. 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 129. (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.
7. 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 129. (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.
8. (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.
9. (b) Shiu, L.-L.; Yu, C. C.; Wong, K.-T.; Chen, B.-L.; Cheng, W.-L.; Yuan, T.-M.; Luh, T.-Y. Organometallics 1993, 12, 1018.
10. (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.
11. (d) Cheng, W.-L.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1992, 1392.
12. (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.
13. (b) Yuan, T.-M.; Luh, T.-Y. J. Org. Chem. 1991, 57, 4550.
14. There is also no evidence to show which metal (magensium or zinc) has been transmetallated, and the exact nature of the nickelabimetallic species 2 or 8 is not known. It is assumed that an organomagnesium compound may be more reactive than the corresponding zinc counterpart (cf. ref 8).
15. Normant, J.-F. Pure Appl. Chem. 1992, 64, 1857.
16. (b) Tucker, C. E.; Greve, B.; Klein, W.; Knochel, P. Organometallics 1994, 13, 94.
17. Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 1039, 1043, 4427, 4431, 5727.
18. Excess amount of the bimetallic reagent 4 was required to give the optimal yield of the coupling product.
19. 1H FT-NMR Spectra, Vol. 1, 42A).