Synthesis of isochromene and related derivatives by rhodium-catalyzed oxidative coupling of benzyl and allyl alcohols with alkynes

Journal of Organic Chemistry

Volumn 76, Issue 22, 2011, Pages 9548-9551

  Morimoto, Keisuke ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOLS; C-H BOND CLEAVAGE; CYCLIC ETHER; HYDROXY GROUPS; ISOCHROMENE DERIVATIVES; OXIDATIVE COUPLINGS; REGIO-SELECTIVE; RHODIUM-CATALYZED;

CATALYSIS; ETHERS; RHODIUM;

ACETYLENE;

1,1 DIMETHYL 3,4 BIS(4 METHYLPHENYL) 1H ISOCHROMENE; 1,1 DIMETHYL 3,4 DIPHENYL 1H BENZO[G]ISOCHROMENE; 1,1 DIMETHYL 3,4 DIPHENYL 1H ISOCHROMENE; 1,1 DIMETHYL 3,4 DIPROPYL 1H ISOCHROMENE; 1,1,3,4 TETRAPHENYL 1H ISOCHROMENE; 1,1,4 TRIMETHYL 3 PHENYL 1H ISOCHROMENE; 1,1,6 TRIMETHYL 3,4 DIPHENYL 1H ISOCHROMENE; 3,4 BIS(4 CHLOROPHENYL) 1,1 DIMETHYL 1H ISOCHROMENE; 3,4 BIS(4 METHOXYPHENYL) 1,1 DIMETHYL 1H ISOCHROMENE; 6 CHLORO 1,1 DIMETHYL 3,4 DIPHENYL 1H ISOCHROMENE; ALKYNE DERIVATIVE; ALLYL ALCOHOL; BENZYL ALCOHOL DERIVATIVE; CHROMENE DERIVATIVE; ISOCHROMENE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; OXIDATIVE COUPLING; SYNTHESIS;

ALKYNES; BENZOPYRANS; BENZYL COMPOUNDS; CATALYSIS; ETHERS, CYCLIC; HYDROGEN BONDING; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROPANOLS; RHODIUM; STEREOISOMERISM;

EID: 81055133624     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201923d     Document Type: Article

References (39)

1. Shishido, Y.; Wakabayashi, H.; Koike, H.; Ueno, N.; Nukui, S.; Yamagishi, T.; Murata, Y.; Naganeo, F.; Mizutani, M.; Shimada, K.; Fujiwara, Y.; Sakakibara, A.; Suga, O.; Kusano, R.; Ueda, S.; Kanai, Y.; Tsuchiya, M.; Satake, K. Bioorg. Med. Chem. 2008, 16, 7193
2. Liu, M.; Xiao, H.-T.; He, H.; Hao, X.-Y. Chem. Nat. Compd. 2008, 44, 588
3. Brown, C. W.; Liu, S.; Klucik, J.; Berlin, K. D.; Brennan, P. J.; Kaur, D.; Benbrook, D. M. J. Med. Chem. 2004, 47, 1008
4. Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284
5. Mutter, R.; Wills, M. Bioorg. Med. Chem. 2000, 8, 1841
6. Larghi, E. L.; Kaufman, T. S. Eur. J. Org. Chem. 2011, 5195
7. Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270
8. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
9. Ackermann, L. Chem. Rev. 2011, 111, 1315
10. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
11. Satoh, T.; Miura, M. Synthesis 2010, 3395
12. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
13. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
14. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
15. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
16. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
17. Thansandote, P.; Lautens, M. Chem.-Eur. J. 2009, 15, 5874
18. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
19. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
20. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
21. Godula, K.; Sames, D. Science 2006, 312, 67
22. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
23. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2011, 40, 600
24. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
25. Mochida, S.; Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. Chem.-Asian J. 2010, 5, 847
26. Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 3478
27. Wei, X.; Zhao, M.; Du, Z.; Li, X. Org. Lett. 2011, 13, 4636
28. Hyster, T. K.; Rovis, T. Chem. Sci. 2011, 2, 1606
29. Wang, Y.-F.; Toh, K. K.; Lee, J.-Y.; Chiba, S. Angew. Chem., Int. Ed. 2011, 50, 5927
30. Patureau, F. W.; Besset, T.; Kuhl, N.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2154
31. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
32. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
33. Uto, T.; Shimizu, M.; Ueura, K.; Tsurugi, H.; Satoh, T.; Miura, M. J. Org. Chem. 2008, 73, 298
34. Liu, Z.-Q.; Zhang, Y.; Zhao, L.; Li, Z.; Wang, J.; Li, H.; Wu, L.-M. Org. Lett. 2011, 13, 2208
35. Mihara, M.; Nakai, T.; Iwai, T.; Ito, T.; Ohno, T.; Mizuno, T. Synlett 2010, 253
36. Howard, F.; Sawadjoon, S.; Samec, J. S. M. Tetrahedron Lett. 2010, 51, 4208
37. Sanz, R.; Martinez, A.; Guilarte, V.; Alvarez-Gutierrez, J. M.; Rodriguez, F. Eur. J. Org. Chem. 2007, 4642
38. Terao, Y.; Wakui, H.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236
39. Novak, Z.; Nemes, P.; Kotschy, A. Org. Lett. 2004, 6, 4917