PtIV-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1055-1058

  Pastine, Stefan J ^a   Youn, So Won ^a   Sames, Dalibor ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AMINE; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; ESTER; ETHER DERIVATIVE; GALLIUM; PALLADIUM; PLATINUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION;

EID: 0042152109     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034177k     Document Type: Article

References (29)

1. (a) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111-112.
2. (b) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692-9693.
3. (c) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586-1587.
4. (d) Baran, P. S.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 7904-7905.
5. Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918.
6. Koch-Pomeranz, U.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 2981-3004.
7. (a) There is yet another mechanistic possibility involving hydro-metalation of triple carbon-carbon bond, generating an alkenylmetal species, followed by intramolecular substitution of the arene ring. Hydropalladation has been proposed to be the first step in the intermolecular cyclization of alkynoate esters and phenols. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1996, 118, 6305-6306.
8. (a) There is yet another mechanistic possibility involving hydro-metalation of triple carbon-carbon bond, generating an alkenylmetal species, followed by intramolecular substitution of the arene ring. Hydropalladation has been proposed to be the first step in the intermolecular cyclization of alkynoate esters and phenols. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1996, 118, 6305-6306.
9. Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516-7522 and references therein.
10. Pei, T.; Wiedenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290-11291.
11. (a) Reference 3.
12. (b) Larock, R. C.; Harrison, L. W. J. Am. Chem. Soc. 1984, 106, 4218-4227.
13. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554.
14. Inoue, H.; Chatani, N,; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
15. (a) Reference 2.
16. (b) Martín-Matute, B.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2001, 40, 4754-4757.
17. (c) Füstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
18. 4-catalyzed addition of carbamates to enones. Kobayashi, S.; Kakumoto, K., Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
19. 4-catalyzed addition of carbamates to enones. Kobayashi, S.; Kakumoto, K., Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
20. 4-catalyzed addition of carbamates to enones. Kobayashi, S.; Kakumoto, K., Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
21. 4-catalyzed addition of carbamates to enones. Kobayashi, S.; Kakumoto, K., Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
22. Apparently, TFA functions at the reductant in this case. It appears that formation of a stabilized cation via protonation of the chromene product is the prerequisite for the subsequent reduction (ester 8a is stable in TFA). We have not been able to find precedent for this transformation.
23. Degner, M.; Holle, B.; Kamm, J.; Pilbrow, M. F.; Thiele, G.; Wagner, D.; Weigel, W.; Woditsch, P. Transition Met. Chem. 1975/76, 1, 41-47.
24. Direct cycloaddition of propargyl alcohols with phenols have been reported. However, these methods do not provide access to chiral chromenes with asymmetric control: (a) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024-7027. (b) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 77900-7901. For other synthetic approaches to chromenes, see: (c) Portscheller, J. L.; Malinakova, H. C. Org. Lett. 2002, 4, 3679-3681 and references therein. For syntheses of fused polycyclic arenes via cyclization of 2-alkynylbiaryls, see: (d) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593 and references therein. (e) Reference 11c.
25. Direct cycloaddition of propargyl alcohols with phenols have been reported. However, these methods do not provide access to chiral chromenes with asymmetric control: (a) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024-7027. (b) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 77900-7901. For other synthetic approaches to chromenes, see: (c) Portscheller, J. L.; Malinakova, H. C. Org. Lett. 2002, 4, 3679-3681 and references therein. For syntheses of fused polycyclic arenes via cyclization of 2-alkynylbiaryls, see: (d) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593 and references therein. (e) Reference 11c.
26. Direct cycloaddition of propargyl alcohols with phenols have been reported. However, these methods do not provide access to chiral chromenes with asymmetric control: (a) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024-7027. (b) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 77900-7901. For other synthetic approaches to chromenes, see: (c) Portscheller, J. L.; Malinakova, H. C. Org. Lett. 2002, 4, 3679-3681 and references therein. For syntheses of fused polycyclic arenes via cyclization of 2-alkynylbiaryls, see: (d) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593 and references therein. (e) Reference 11c.
27. Direct cycloaddition of propargyl alcohols with phenols have been reported. However, these methods do not provide access to chiral chromenes with asymmetric control: (a) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024-7027. (b) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 77900-7901. For other synthetic approaches to chromenes, see: (c) Portscheller, J. L.; Malinakova, H. C. Org. Lett. 2002, 4, 3679-3681 and references therein. For syntheses of fused polycyclic arenes via cyclization of 2-alkynylbiaryls, see: (d) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593 and references therein. (e) Reference 11c.
28. Direct cycloaddition of propargyl alcohols with phenols have been reported. However, these methods do not provide access to chiral chromenes with asymmetric control: (a) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024-7027. (b) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 77900-7901. For other synthetic approaches to chromenes, see: (c) Portscheller, J. L.; Malinakova, H. C. Org. Lett. 2002, 4, 3679-3681 and references therein. For syntheses of fused polycyclic arenes via cyclization of 2-alkynylbiaryls, see: (d) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593 and references therein. (e) Reference 11c.
29. Chisholm, M. H.; Clark, H. C. Acc. Chem. Res. 1973, 6, 202-209.