Organocatalytic chemo- and regioselective oxyarylation of styrenes via a cascade reaction: Remote activation of hydroxyl groups

Journal of Organic Chemistry

Volumn 79, Issue 13, 2014, Pages 6143-6152

  Zhang, Yu Chen ^a   Jiang, Fei ^a   Wang, Shu Liang ^a   Shi, Feng ^a   Tu, Shu Jiang ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL ACTIVATION; HYDROGEN BONDS; REACTION KINETICS; REGIOSELECTIVITY;

CASCADE REACTIONS; CONJUGATIVE EFFECT; DIASTEREO-SELECTIVITY; HYDROGEN BONDING INTERACTIONS; HYDROXYL FUNCTIONALITY; REACTION PATHWAYS; REMOTE ACTIVATION; TRANSFER REACTION;

STYRENE;

BENZYL [3 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]BENZAMIDE; HYDROXYL GROUP; N [3 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]ACETAMIDE; N [3 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]BENZAMIDE; PHOSPHORIC ACID; STYRENE DERIVATIVE; TER BUTYL [3 [2 (5 TERT BUTYL} 2 HYDROXYPHENYL] 2 METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 CHLORO [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXY 5 METHOXYPHENYL) 2METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXY 5 METHYLPHENYL) 2METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXYPHENYL) 2 ISOPROPOXYETHYL] 4 ISOPROPOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXY 5 METHYLPHENYL ]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 5 IODO 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (2 HYDROXYPHENYL) 2 METHOXYPROPYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (5 BROMO 2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (5 CHLORO 2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [3 [2 (5 FLUORO 2 HYDROXYPHENYL) 2 METHOXYETHYL] 4 METHOXYPHENYL]CARBAMATE; TERT BUTYL [4 BUTOXY 3 [2 BUTOXY 2 (2 HYDROXYPHENYL)ETHYL] PHENYL]CARBAMATE; TERT BUTYL [4 ETHOXY 3 [2 ETHOXY 2 (2 HYDROXYPHENYL)ETHYL] PHENYLCARBAMATE; TERT BUTYL [5 [2 (2 HYDROXYPHENYL) 2 METHOXYETHYL] 6 METHOXY [1,1' BIPHENYL] 3 YL]CARBAMATE; UNCLASSIFIED DRUG; HYDROXYL RADICAL; NAPHTHALENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; HYDROGEN BOND; MICHAEL ADDITION; OXYARYLATION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; HYDROGEN BONDING; HYDROXYL RADICAL; MOLECULAR STRUCTURE; NAPHTHALENES; PHOSPHORIC ACIDS; STEREOISOMERISM; STYRENES;

EID: 84903721596     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500859b     Document Type: Article

References (42)

1. Haldar, S.; Koner, S. J. Org. Chem. 2010, 75, 6005
2. Gligorich, K. M.; Cummings, S. A.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 14193
3. Liang, X.; George, S. M.; Weimer, A. W.; Li, N.-H.; Blackson, J. H.; Harris, J. D.; Li, P. Chem. Mater. 2007, 19, 5388
4. Dong, J. Y.; Manias, E.; Chung, T. C. Macromolecules 2002, 35, 3439
5. Heck, R. F. Acc. Chem. Res. 1979, 12, 146
6. Daves, G. D.; Hallberg, A. Chem. Rev. 1989, 89, 1433
7. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
8. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
9. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644
10. Ruan, J.; Xiao, J. Acc. Chem. Res. 2011, 44, 614
11. Mc Cartney, D.; Guiry, P. J. Chem. Soc. Rev. 2011, 40, 5122
12. Sigman, M. S.; Werner, E. W. Acc. Chem. Res. 2012, 45, 874
13. Monfette, S.; Fogg, D. E. Chem. Rev. 2009, 109, 3783
14. van Otterlo, W. A. L.; de Koning, C. B. Chem. Rev. 2009, 109, 3743
15. Choi, S.-K.; Gal, Y.-S.; Jin, S.-H.; Kim, H. K. Chem. Rev. 2000, 100, 1645
16. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199
17. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239
18. Hartmann, M.; Li, Y.; Studer, A. J. Am. Chem. Soc. 2012, 134, 16516
19. Ball, L. T.; Lloyd-Jones, G. C.; Russell, C. A. Chem.-Eur. J. 2012, 18, 2931
20. Fumagalli, G.; Boyd, S.; Greaney, M. F. Org. Lett. 2013, 15, 4398
21. Wang, L.; Fan, R. Org. Lett. 2012, 14, 3596
22. Satterfield, A. D.; Kubota, A.; Sanford, M. S. Org. Lett. 2011, 13, 1076
23. Urbano, J.; Hormigo, A. J.; Fremont, P. D.; Nolan, S. P.; Diaz-Requejo, M. M.; Perez, P. J. Chem. Commun. 2008, 759
24. Chen, C.-P.; Chou, C.-T.; Swenton, J. S. J. Am. Chem. Soc. 1987, 109, 946
25. Swenton, J. S.; Bonke, B. R.; Clark, W. M.; Chen, C.-P.; Martin, K. V. J. Org. Chem. 1990, 55, 2027
26. Dalidowicz, P.; Swenton, J. S. J. Org. Chem. 1993, 58, 4802
27. Banfield, S. C.; England, D. B.; Kerr, M. A. Org. Lett. 2001, 3, 3325
28. Chuang, K. V.; Navarro, R.; Reisman, S. E. Chem. Sci. 2011, 2, 1086
29. Dohi, T.; Hu, Y.; Kamitanaka, T.; Washimi, N.; Kita, Y. Org. Lett. 2011, 13, 4814
30. Hu, Y.; Kamitanaka, T.; Mishima, Y.; Dohi, T.; Kita, Y. J. Org. Chem. 2013, 78, 5530
31. Hashimoto, T.; Nakatsu, H.; Takiguchi, Y.; Maruoka, K. J. Am. Chem. Soc. 2013, 135, 16010
32. Akiyama, T. Chem. Rev. 2007, 107, 5744
33. Terada, M. Chem. Commun. 2008, 35, 4097
34. Terada, M. Synthesis 2010, 1929
35. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156
36. Shi, F.; Xing, G.-J.; Zhu, R.-Y.; Tan, W.; Tu, S.-J. Org. Lett. 2013, 15, 128
37. Shi, F.; Tan, W.; Zhu, R.-Y.; Xing, G.-J.; Tu, S.-J. Adv. Synth. Catal. 2013, 355, 1605
38. Shi, F.; Zhu, R.-Y.; Dai, W.; Wang, C.-S.; Tu, S.-J. Chem.-Eur. J. 2014, 20, 2597
39. Sajiki, H.; Mori, A.; Mizusaki, T.; Ikawa, T.; Maegawa, T.; Hirota, K. Org. Lett. 2006, 8, 987
40. Jensen, K. L.; Franke, P. T.; Nielsen, L. T.; Daasbjerg, K.; Jøgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 129
41. Elias, X.; Pleixats, R.; Man, M. W. C. Tetrahedron 2008, 64, 6770
42. Chatterjee, A. K.; Toste, F. D.; Goldberg, S. D.; Grubbs, R. H. Pure Appl. Chem. 2003, 75, 421