Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins

Organic Letters

Volumn 17, Issue 19, 2015, Pages 4850-4853

  Hara, Yusuke ^a   Onodera, Shunsuke ^a   Kochi, Takuya ^a   Kakiuchi, Fumitoshi ^a,b  

^a KEIO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBONIC ACID DERIVATIVE; ISOCOUMARIN 3; ISOCOUMARIN DERIVATIVE; KETONE; NITROGEN; RHODIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKENES; CARBONATES; CATALYSIS; CYCLIZATION; ISOCOUMARINS; KETONES; MOLECULAR STRUCTURE; NITROGEN; RHODIUM;

EID: 84942897635     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02414     Document Type: Article

References (46)

1. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234 10.1021/ar0201106
2. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082 10.1021/cr9000836
3. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676 10.1002/anie.200903424
4. Novak, P.; Martin, R. Curr. Org. Chem. 2011, 15, 3233 10.2174/138527211797248021
5. Yu, X.; Yu, S.; Xiao, J.; Wan, B.; Li, X. J. Org. Chem. 2013, 78, 5444 10.1021/jo400572h
6. Shi, J.; Yan, Y.; Li, Q.; Xu, H. E.; Yi, W. Chem. Commun. 2014, 50, 6483 10.1039/c4cc01593b
7. Jeong, J.; Patel, P.; Hwang, H.; Chang, S. Org. Lett. 2014, 16, 4598 10.1021/ol502173d
8. Ai, W.; Yang, X.; Wu, Y.; Wang, X.; Li, Y.; Yang, Y.; Zhou, B. Chem.-Eur. J. 2014, 20, 17653 10.1002/chem.201405077
9. Xia, Y.; Liu, Z.; Feng, S.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 223 10.1021/jo5023102
10. Chan, W.-W.; Zhou, Z.; Yu, W.-Y. Chem. Commun. 2013, 49, 8214 10.1039/c3cc44769c
11. Zhang, X.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2014, 53, 10794 10.1002/anie.201406747
12. Sharma, U.; Park, Y.; Chang, S. J. Org. Chem. 2014, 79, 9899 10.1021/jo501995c
13. Yu, D.-G.; de Azambuja, F.; Glorius, F. Angew. Chem., Int. Ed. 2014, 53, 2754 10.1002/anie.201310272
14. Zhu, C.; Falck, J. R. Chem. Commun. 2012, 48, 1674 10.1039/C2CC16963K
15. Zhu, C.; Falck, J. R. Tetrahedron 2012, 68, 9192 10.1016/j.tet.2012.08.095
16. Cui, S.; Zhang, Y.; Wang, D.; Wu, Q. Chem. Sci. 2013, 4, 3912 10.1039/c3sc51777b
17. Lam, H.-W.; Man, K.-Y.; Chan, W.-W.; Zhou, Z.; Yu, W.-Y. Org. Biomol. Chem. 2014, 12, 4112 10.1039/c4ob00512k
18. Ye, B.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 7896 10.1002/anie.201404895
19. Shi, J.; Zhou, J.; Yan, Y.; Jia, J.; Liu, X.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 668 10.1039/C4CC08407A
20. Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X. J. Am. Chem. Soc. 2015, 137, 1623 10.1021/ja511796h
21. Li, X. G.; Sun, M.; Liu, K.; Jin, Q.; Liu, P. N. Chem. Commun. 2015, 51, 2380 10.1039/C4CC09314C
22. Wang, H.-L.; Shang, M.; Sun, S.-Z.; Zhou, Z.-L.; Laforteza, B. N.; Dai, H.-X.; Yu, J.-Q. Org. Lett. 2015, 17, 1228 10.1021/acs.orglett.5b00193
23. Zhang, S.-S.; Wu, J.-Q.; Lao, Y.-X.; Liu, X.-G.; Liu, Y.; Lv, W.-X.; Tan, D.-H.; Zeng, Y.-F.; Wang, H. Org. Lett. 2014, 16, 6412 10.1021/ol503229c
24. Zhang, S.-S.; Wu, J.-Q.; Liu, X.; Wang, H. ACS Catal. 2015, 5, 210 10.1021/cs501601c
25. Matsuura, Y.; Tamura, M.; Kochi, T.; Sato, M.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 9858 10.1021/ja071965m
26. Ogiwara, Y.; Tamura, M.; Kochi, T.; Matsuura, Y.; Chatani, N.; Kakiuchi, F. Organometallics 2014, 33, 402 10.1021/om401204h
27. Ogiwara, Y.; Kochi, T.; Kakiuchi, F. Chem. Lett. 2014, 43, 667 10.1246/cl.140006
28. Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173 10.1021/jo00057a033
29. Toullec, P.; Martin, A. C.; Gio-Batta, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 2000, 41, 5527 10.1016/S0040-4039(00)00889-3
30. Bigovic, M.; Skaro, S.; Maslak, V.; Saicic, R. N. Tetrahedron Lett. 2013, 54, 6624 10.1016/j.tetlet.2013.09.115
31. Fournier, J.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 1989, 30, 3981 10.1016/S0040-4039(00)99300-6
32. Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515 10.1021/ol053100o
33. Buzas, A. K.; Istrate, F. M.; Gagosz, F. Tetrahedron 2009, 65, 1889 10.1016/j.tet.2008.11.108
34. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624 10.1021/cr900005n
35. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212 10.1002/chem.201001363
36. Patureau, F. W.; Wencel-Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31
37. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651 10.1039/c2cs15281a
38. Zhang, X.-S.; Chen, K.; Shi, Z.-J. Chem. Sci. 2014, 5, 2146 10.1039/c3sc53115e
39. Wang, L.; Ackermann, L. Chem. Commun. 2014, 50, 1083 10.1039/C3CC47852A
40. Schröder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298 10.1021/ja302631j
41. Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274 10.1021/ja00330a041
42. Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211 10.1021/jo980584b
43. Nandi, D.; Ghosh, D.; Chen, S.-J.; Kuo, B.-C.; Wang, N. M.; Lee, H. M. J. Org. Chem. 2013, 78, 3445 10.1021/jo400174w
44. Many examples of transition-metal-catalyzed formation of 3,4-disubstituted isocoumarins via C-H bond cleavage have been reported. For a pioneering study, see: Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407 10.1021/ol070406h
45. Kurume, A.; Kamata, Y.; Yamashita, M.; Wang, Q.; Matsuda, H.; Yoshikawa, M.; Kawasaki, I.; Ohta, S. Chem. Pharm. Bull. 2008, 56, 1264 10.1248/cpb.56.1264
46. The highly electrophilic nature of dicationic Rh(III) species A may prevent the catalyst from reacting with the cyclic alkenyl carbonate and forming an oxatrimethylenemethane complex. For the formation of oxatrimethylenemethane palladium complexes from cyclic alkenyl carbonates, see: Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173 10.1021/jo00057a033