Hydroarylation of acetylenes, acrylates, and isocyanates with heteroaromatic compounds under rhenium catalysis

Tetrahedron

Volumn 64, Issue 26, 2008, Pages 5974-5981

  Kuninobu, Yoichiro ^a   Kikuchi, Kou ^a   Tokunaga, Yukimi ^a   Nishina, Yuta ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ACRYLIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; RHENIUM;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 43849105130     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.145     Document Type: Article

References (26)

1. In: Meth-Cohn O. (Ed). Comprehensive Heterocyclic Chemistry Vol. 1 (1984), Pergamon, New York, NY
2. In: Bird C.W., and Cheeseman G.W.H. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1984), Pergamon, New York, NY
3. Katritzky A.R., and Pozharskii A.F. Handbook of Heterocyclic Chemistry. 2nd ed. (2000), Pergamon, Oxford
4. For the reviews, see:
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7. Tsuji J., and Nagashima H. Tetrahedron 40 (1984) 2699
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12. Fukumoto Y., Sawada K., Hagihara M., Chatani N., and Murai S. Angew. Chem., Int. Ed. 41 (2002) 2779
13. We have also reported the amidation hydroarylation of heteroaromatic compounds via C-H bond activation. See:. Kuninobu Y., Tokunaga Y., and Takai K. Chem. Lett. 36 (2007) 872
14. For intramolecular hydroarylation of an olefin moiety, see:. Tan K.L., Bergman R.G., and Ellman J.A. J. Am. Chem. Soc. 124 (2002) 3202
15. For our recent reports on rhenium-catalyzed functionalizations via C-H bond activation of a benzene ring, see:
16. Kuninobu Y., Kawata A., and Takai K. J. Am. Chem. Soc. 127 (2005) 13498
17. Kuninobu Y., Tokunaga Y., Kawata A., and Takai K. J. Am. Chem. Soc. 128 (2006) 202
18. Kuninobu Y., Nishina Y., Shouho M., and Takai K. Angew. Chem., Int. Ed. 45 (2006) 2766
19. Kuninobu Y., Nishina Y., Nakagawa C., and Takai K. J. Am. Chem. Soc. 128 (2006) 12376
20. Investigation of solvents: dioxane, 34%; THF, 45%; hexane, 67%; 1,2-dichloroethane, 76%; toluene, 76%.
21. Investigation of reaction temperature: 25 °C, 0%; 50 °C, 14%; 70 °C, 33%; 90 °C, 76%.
22. Investigation of reaction time: 1 h, 19%; 3 h, 47%; 8 h, 52%; 24 h, 76%.
23. There has been a report on whether the hydroarylation occurs at the 4-position of heteroaromatic compounds; however, the reaction did not proceed. See:. Kakiuchi F., Sekine S., Tanaka Y., Kamatani A., Sonoda M., Chatani N., and Murai S. Bull. Chem. Soc. Jpn. 68 (1995) 62
24. There has been a report on the hydroarylation of an alkynoate at 4-position with pyrroles. See:. Oyamada J., Lu W., Jia C., Kitamura T., and Fujiwara Y. Chem. Lett. (2002) 20
25. + are formed as intermediates. When we examined the rhenium-catalyzed amidation in the presence of tributylamine as a Lewis base, the reaction proceeded without decreasing the yield. Thus, we are tempted to assume that this reaction proceeds via C-H bond activation.
26. Insertion of unsaturated molecules into an Re-H bond followed by reductive elimination can also give the same product; however, we have observed that the insertion into an Re-C bond occurs faster. See Ref. 11.