Complete regioselection in palladium-catalyzed arylation and alkenylation of allylic alcohols with hypervalent iodonium salts

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2604-2605

  Kang, Suk Ku ^a   Lee, Hong Woo ^a   Jang, Su Bum ^a   Kim, Tae Hyun ^a   Pyun, Sung Jae ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000882877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951923t     Document Type: Article

References (32)

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18. For recent reviews: (a) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (b) Moriarty, R. M.; Viad, R. K. Synthesis 1990, 431. (c) Ochiai, M. Rev. Heteroatom. Chem. 1989, 2, 92.
19. For recent reviews: (a) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (b) Moriarty, R. M.; Viad, R. K. Synthesis 1990, 431. (c) Ochiai, M. Rev. Heteroatom. Chem. 1989, 2, 92.
20. Pd-catalyzed C-C bond formation: (a) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315. (b) Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095. (c) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626. (d) Kang, S.-K.; Jung, K. Y., Park, C.-H.: Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047.
21. Pd-catalyzed C-C bond formation: (a) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315. (b) Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095. (c) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626. (d) Kang, S.-K.; Jung, K. Y., Park, C.-H.: Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047.
22. Pd-catalyzed C-C bond formation: (a) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315. (b) Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095. (c) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626. (d) Kang, S.-K.; Jung, K. Y., Park, C.-H.: Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047.
23. Pd-catalyzed C-C bond formation: (a) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315. (b) Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095. (c) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626. (d) Kang, S.-K.; Jung, K. Y., Park, C.-H.: Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047.
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27. 2O without using base cinnamyl alcohol (4) was obtained in 71% yield, although the reaction was not clean.
28. In the literature, the coupling of alkenyl(phenyl)iodonium salts with olefins, 3 equiv of olefins were used. See ref 8a. In the palladium-catalyzed cross-coupling of alkenyl (phenyl)iodonium salts with organotin compounds, for the iodonium salts excess organotin compounds were used. See ref 8b.
29. Diphenyliodonium and alkenyl(phenyl)iodonium triflates can be used. In our hands, with tetrafluoroborate the reactions were more clean.
30. 2 was the most effective. The reaction could be carried out without base. However, we could not get a higher yield in the absence of the base.
31. Drew, J.; Letellier, M.; Morand, P.; Szabo, A. G. J Org. Chem. 1987, 52, 4047
32. 6 equation presented