Rh(I)-catalyzed direct ortho-alkenylation of aromatic ketimines with alkynes and its application to the synthesis of isoquinoline derivatives

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2759-2761

  Lim, Sung Gon ^a   Lee, Jun Hee ^a   Moon, Choong Woon ^a   Hong, Jun Bae ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALKYNE DERIVATIVE; BENZYLAMINE DERIVATIVE; IMINE; ISOQUINOLINE DERIVATIVE; KETONE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141855014     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035083d     Document Type: Article

References (24)

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10. (a) Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485.
11. (b) Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-Y. Angew. Chem., Int. Ed. 2000, 39, 3440.
12. (a) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681.
13. For the site selective vinylation of aromatic compounds, see: (b) Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053. (c) Harris, P. W. R.; Rickard, C. E. F.; Woodgate, P. D. J. Organomet. Chem. 1999, 589, 168. Also see: (d) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
14. For the site selective vinylation of aromatic compounds, see: (b) Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053. (c) Harris, P. W. R.; Rickard, C. E. F.; Woodgate, P. D. J. Organomet. Chem. 1999, 589, 168. Also see: (d) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
15. For the site selective vinylation of aromatic compounds, see: (b) Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053. (c) Harris, P. W. R.; Rickard, C. E. F.; Woodgate, P. D. J. Organomet. Chem. 1999, 589, 168. Also see: (d) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
16. For β-vinylation of α,β-unsaturated ketone with internal alkynes, see: Kakiuchi, F.; Uetsuhara, T.; Tanaka, Y.; Chatani, N.; Murai, S. J. Mol. Catal. A: Chem. 2002, 182-183, 511.
17. ortho-Arylation of aromatic ketones using arylboronates also has been reported very recently: Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
18. Rh(I)-catalyzed ortho-vinylation of some 2-phenylpyridine derivatives with only internal alkynes has been reported: Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Tetrahedron Lett. 2001, 42, 7609.
19. Attempts to hydrolyze the 2,4-dialkenylated ketimines 5 failed.
20. The stereochemistry of 4 and 5 was deduced from the proposed mechanism (Figure 1) and confirmed to be all-trans by measuring the coupling constant between two olefinic protons of the products only except for 4ai.
21. Recently, Larock and co-workers ingeniously utilized Pd-catalyzed tandem cross coupling of the tert-butylimine of o-iodobenzaldehyde with alkynes-iminoannulation sequence to synthesize a variety of 3,4-disubstituted isoquinoline derivatives: (a) Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306. Also see: (b) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437 and references therein.
22. Recently, Larock and co-workers ingeniously utilized Pd-catalyzed tandem cross coupling of the tert-butylimine of o-iodobenzaldehyde with alkynes-iminoannulation sequence to synthesize a variety of 3,4-disubstituted isoquinoline derivatives: (a) Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306. Also see: (b) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437 and references therein.
23. The structure of 10a has been confirmed undoubtedly by the independent synthesis of 10a from 9a. See Supporting Information.
24. When the reaction of 1a with 2i was performed for a short period of reaction time (e.g., for 2 h), a small amount of 16a and 18a (R = H) was isolated and characterized spectroscopically. See Supporting Information.