Practical Pd(II)-Catalyzed C-H Alkylation with Epoxides: One-Step Syntheses of 3,4-Dihydroisocoumarins

Journal of the American Chemical Society

Volumn 137, Issue 34, 2015, Pages 10950-10953

  Cheng, Guolin ^a   Li, Tuan Jie ^a   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; BENZOIC ACID; CATALYSIS;

ALKYLATION REACTIONS; NUCLEOPHILIC RING OPENING; ONE STEP SYNTHESIS; PD CATALYST;

PALLADIUM COMPOUNDS;

3,4 DIHYDROISOCOUMARIN DERIVATIVE; AMINO ACID; BENZOIC ACID DERIVATIVE; EPOXIDE; ISOCOUMARIN DERIVATIVE; PALLADIUM; POTASSIUM; SOLVENT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; HYDROGEN BOND; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 84940971187     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b07507     Document Type: Article

References (66)

1. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077 10.1002/adsc.200303094
2. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094 10.1002/anie.200806273
3. Ackermann, L. Chem. Commun. 2010, 46, 4866 10.1039/c0cc00778a
4. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 10.1021/cr900184e
5. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814 10.1021/ar200190g
6. Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550 10.1002/anie.200301679
7. Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903 10.1021/cr078372e
8. Bandini, M.; Tragni, M. Org. Biomol. Chem. 2009, 7, 1501 10.1039/b823217b
9. Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634 10.1021/ja0646747
10. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882 10.1002/anie.200801030
11. Thuy-Boun, P. S.; Villa, G.; Dang, D.; Richardson, P.; Su, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 17508 10.1021/ja409014v
12. Neufeldt, S. R.; Seigerman, C. K.; Sanford, M. S. Org. Lett. 2013, 15, 2302 10.1021/ol400888r
13. Tremont, S. J.; Rahman, H. u. J. Am. Chem. Soc. 1984, 106, 5759 10.1021/ja00331a073
14. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 6097 10.1002/anie.200902262
15. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965 10.1021/ja910900p
16. Zhao, Y.; Chen, G. Org. Lett. 2011, 13, 4850 10.1021/ol201930e
17. Xiao, B.; Liu, Z.-J.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 616 10.1021/ja3113752
18. Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2015, 137, 531 10.1021/ja511557h
19. Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed. 2012, 51, 5188 10.1002/anie.201200731
20. Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.-S.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124 10.1021/ja312277g
21. Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135 10.1021/ja406484v
22. Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906 10.1039/c3sc51747k
23. Zhu, R.-Y.; He, J.; Wang, X.-C.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 13194 10.1021/ja508165a
24. Chen, K.; Shi, B.-F. Angew. Chem., Int. Ed. 2014, 53, 11950 10.1002/anie.201407848
25. Vechorkin, O.; Proust, V.; Hu, X. Angew. Chem., Int. Ed. 2010, 49, 3061 10.1002/anie.200907040
26. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308 10.1021/ja401344e
27. Song, W.; Lackner, S.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 2477 10.1002/anie.201309584
28. Wu, X.-S.; Zhao, Y.; Ge, H.-B. J. Am. Chem. Soc. 2014, 136, 1789 10.1021/ja413131m
29. Ackermann, L.; Novak, P.; Vicente, R.; Hofmann, N. Angew. Chem., Int. Ed. 2009, 48, 6045 10.1002/anie.200902458
30. Hofmann, N.; Ackermann, L. J. Am. Chem. Soc. 2013, 135, 5877 10.1021/ja401466y
31. Chen, Q.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 428 10.1021/ja1099853
32. Punji, B.; Song, W.; Shevchenko, G. A.; Ackermann, L. Chem.-Eur. J. 2013, 19, 10605 10.1002/chem.201301409
33. Gao, K.; Yoshikai, N. J. Am. Chem. Soc. 2013, 135, 9279 10.1021/ja403759x
34. Ilies, L.; Matsubara, T.; Ichikawa, S.; Asako, S.; Nakamura, E. J. Am. Chem. Soc. 2014, 136, 13126 10.1021/ja5066015
35. Fruchey, E. R.; Monks, B. M.; Cook, S. P. J. Am. Chem. Soc. 2014, 136, 13130 10.1021/ja506823u
36. Monks, B. M.; Fruchey, E. R.; Cook, S. P. Angew. Chem., Int. Ed. 2014, 126, 11065 10.1002/anie.201406594
37. Deng, G.; Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 6278 10.1002/anie.200801544
38. Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2011, 50, 2990 10.1002/anie.201007733
39. Lee, D.-H.; Kwon, K.-H.; Yi, C. S. Science 2011, 333, 1613 10.1126/science.1208839
40. Makida, Y.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2012, 51, 4122 10.1002/anie.201200809
41. Tamura, R.; Yamada, Y.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2012, 51, 5679 10.1002/anie.201200922
42. Ma, S.; Villa, G.; Thuy-Boun, P. S.; Homs, A.; Yu, J.-Q. Angew. Chem., Int. Ed. 2014, 53, 734 10.1002/anie.201305388
43. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411 10.1002/(SICI)1521-3773(19990816)38:16<2411::AID-ANIE2411>3.0.CO;2-T
44. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020 10.1021/ja0002058
45. Wang, Z.; Kuninobu, Y.; Kanai, M. J. Am. Chem. Soc. 2015, 137, 6140 10.1021/jacs.5b02435
46. Hojo, D.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2008, 47, 5820 10.1002/anie.200801642
47. Rioz-Martinez, A.; de Gonzalo, G.; Torres Pazmino, D. E.; Fraaije, M. W.; Gotor, V. J. Org. Chem. 2010, 75, 2073 10.1021/jo902519j
48. Fujita, M.; Mori, K.; Shimogaki, M.; Sugimura, T. Org. Lett. 2012, 14, 1294 10.1021/ol300185u
49. Chen, J.; Zhou, L.; Tan, C. K.; Yeung, Y.-Y. J. Org. Chem. 2012, 77, 999 10.1021/jo202221c
50. Aspin, S.; Lopez-Suarez, L.; Larini, P.; Goutierre, A.-S.; Jazzar, R.; Baudoin, O. Org. Lett. 2013, 15, 5056 10.1021/ol402398s
51. Mangas-Sanchez, J.; Busto, E.; Gotor, V.; Gotor-Fernandez, V. Org. Lett. 2013, 15, 3872 10.1021/ol401606x
52. Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510 10.1021/ja0701614
53. Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082 10.1021/ja8063827
54. Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 5215 10.1002/anie.200705613
55. Engle, K. M.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137 10.1021/ja105044s
56. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315 10.1126/science.1182512
57. Zhu, C.; Zhang, Y.; Kan, J.; Zhao, H.; Su, W. Org. Lett. 2015, 17, 3418 10.1021/acs.orglett.5b01398
58. Pineschi, M. Eur. J. Org. Chem. 2006, 2006, 4979 10.1002/ejoc.200600384
59. Huang, C.-Y.; Doyle, A. G. Chem. Rev. 2014, 114, 8153 10.1021/cr500036t
60. Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579 10.1021/jo00069a017
61. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089 10.1016/S0040-4039(99)00656-5
62. Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343 10.1002/1521-3773(20021115)41:22<4343::AID-ANIE4343>3.0.CO;2-5
63. Sole, D.; Vallverdu, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587 10.1021/ja029114w
64. Jia, Y.-X.; Katayev, D.; Kündig, E. P. Chem. Commun. 2010, 46, 130 10.1039/B917958E
65. Yin, L.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2011, 50, 7620 10.1002/anie.201102158
66. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462 10.1002/anie.200804153