The oxidative annulation of tertiary benzyl alcohols with internal alkynes using an (electron-deficient η5-cyclopenta-dienyl)rhodium(III) catalyst under ambient conditions

Advanced Synthesis and Catalysis

Volumn 356, Issue 7, 2014, Pages 1638-1644

  Fukui, Miho ^a   Hoshino, Yuki ^a   Satoh, Tetsuya ^b,c   Miura, Masahiro ^b   Tanaka, Ken ^a,c  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

alkynes; annulation; benzyl alcohols; C H bond functionalization; rhodium

Indexed keywords

EID: 84900459235     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400084     Document Type: Article

References (39)

1. E. Peris, P. Lahuerta, in: Comprehensive Organometallic Chemistry III, Vol. 7, (Eds.:, H. C. Robert, D. M. P. Mingos,), Elsevier, Oxford, 2007, p 139
2. P. M. Maitlis, J. Organomet. Chem. 1995, 500, 239.
3. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
4. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31
5. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814
6. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212
7. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013.
8. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474
9. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326.
10. J. Wencel-Delord, C. Nimphius, H. Wang, F. Glorius, Angew. Chem. 2012, 124, 13175
11. Angew. Chem. Int. Ed. 2012, 51, 13001
12. H. Wang, C. Grohmann, C. Nimphius, F. Glorius, J. Am. Chem. Soc. 2012, 134, 19592
13. T.-S. Jiang, G.-W. Wang, J. Org. Chem. 2012, 77, 9504
14. B. Schmidt, N. Elizarov, Chem. Commun. 2012, 48, 4352
15. B. Xiao, Y.-M. Li, Z.-J. Liu, H.-Y. Yang, Y. Fu, Chem. Commun. 2012, 48, 4854
16. F. Zhou, X. Han, X. Lu, Tetrahedron Lett. 2011, 52, 4681
17. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem. 2011, 123, 1374
18. Angew. Chem. Int. Ed. 2011, 50, 1338
19. Y. Su, M. Zhao, G. Song, X. Li, Org. Lett. 2010, 12, 5462
20. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
21. R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593
22. Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007, 119, 5650
23. Angew. Chem. Int. Ed. 2007, 46, 5554
24. S. Yang, B. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 6066
25. X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, Z. Shi, J. Am. Chem. Soc. 2006, 128, 7416
26. V. G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156.
27. Y. Shibata, K. Tanaka, Angew. Chem. 2011, 123, 11109
28. Angew. Chem. Int. Ed. 2011, 50, 10917. As a related cyclotrimerization reaction, our research group reported the synthesis of substituted dihydropentalenes by the rhodium-catalyzed cross-cyclotrimerization of propargyl esters and two arylacetylenes. See
29. Y. Shibata, K. Noguchi, K. Tanaka, Org. Lett. 2010, 12, 5596.
30. 2) in the oxidative pyridine synthesis, while both the product yield and regioselectivity were low. See:, T. K. Hyster, T. Rovis, Chem. Commun. 2011, 47, 11846.
31. Y. Hoshino, Y. Shibata, K. Tanaka, Adv. Synth. Catal. 2014, 356, 1577-1585.
32. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982
33. Y. Wang, C. Li, Y. Li, F. Yin, X.-S. Wang, Adv. Synth. Catal. 2013, 355, 1724.
34. K. Morimoto, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 9548.
35. T. Uto, M. Shimizu, K. Ueura, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 298. For the oxidative annulation of 1-naphthols or 1-hydroxyisoquinoline with alkynes, see
36. S. Mochida, M. Shimizu, K. Hirano, T. Satoh, M. Miura, Chem. Asian J. 2010, 5, 847
37. G. Song, D. Chen, C.-L. Pan, R. H. Crabtree, X. Li, J. Org. Chem. 2010, 75, 7487.
38. The palladium-catalyzed arylation of α,α-disubstituted arylmethanols via cleavage of a C-C or a C-H bond has been reported, see:, Y. Terao, H. Wakui, M. Nomoto, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 5236.
39. For a review of the metal-catalyzed C-H bond activation under mild conditions, see:, J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740.