Palladium(II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates

Journal of Organic Chemistry

Volumn 78, Issue 22, 2013, Pages 11247-11254

  Meng, Xiangjian ^a   Kim, Sunggak ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; DIRECTING GROUPS; HIGH YIELD; MONOESTERS; PHOSPHONIC;

AROMATIC COMPOUNDS; CATALYSIS; FUNCTIONAL GROUPS; POTASSIUM;

PALLADIUM COMPOUNDS;

BENZILIC ACID DERIVATIVE; BORIC ACID; FUNCTIONAL GROUP; PALLADIUM; PHOSPHONIC ACID DERIVATIVE; POTASSIUM;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION;

BENZYL COMPOUNDS; BORATES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHOROUS ACIDS; POTASSIUM;

EID: 84887866930     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401716p     Document Type: Article

References (71)

1. Balzarini, J.; Holy, A.; Jindrich, J.; Naesens, L.; Snoeck, R.; Schols, D.; De Clercq, E. Antimicrob. Agents Chemother. 1993, 37, 332
2. McCarthy, M.; Guiry, P. J. Tetrahedron 2001, 57, 3809
3. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029
4. Khandelwal, A.; Lukacova, V.; Comez, D.; Kroll, D. M.; Raha, S.; Balaz, S. J. Med. Chem. 2005, 48, 5437
5. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
6. Metcalf, W. W.; van der Donk, W. A. Annu. Rev. Biochem. 2009, 78, 65
7. Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981
8. Queffélec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777
9. Yoshino, K.; Goto, K.; Yoshiizumi, K.; Morita, T.; Tsukamoto, G. J. Med. Chem. 1990, 33, 2192
10. de Garavilla, L.; Greco, M. N.; Sukumar, N.; Chen, Z.-W.; Pineda, A. O.; Mathews, F. S.; Di Cera, E.; Giardino, E. C.; Wells, G. I.; Haertlein, B. J.; Kauffman, J. A.; Corcoran, T. W.; Derian, C. K.; Eckardt, A. J.; Damiano, B. P.; Andrade-Gordon, P.; Maryanoff, B. E. J. Biol. Chem. 2005, 280, 18001
11. Wardworth, W. S., Jr. Org. React. 1977, 25, 73
12. Stec, W. J. Acc. Chem. Res. 1983, 16, 411
13. Bisceglia, J. A.; Orelli, L. R. Curr. Org. Chem. 2012, 16, 2206
14. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
15. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
16. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
17. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
18. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
19. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
20. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
21. Ackermann, L. Chem. Rev. 2011, 111, 1315
22. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450
23. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
24. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
25. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
26. Wencel-Delord, J.; Glorius, F. Nature Chem. 2013, 5, 369
27. Satoh, T.; Miura, M. Synthesis 2010, 3395
28. Zhao, X.; Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 5837
29. Nishikata, T.; Abela, A. R.; Huang, S.; Lipshutz, B. H. J. Am. Chem. Soc. 2010, 132, 4978
30. Feng, C.; Loh, T. P. Chem. Commun. 2011, 47, 10458
31. Park, S. H.; Kim, J. Y.; Chang, S. Org. Lett. 2011, 13, 2372
32. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064
33. Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728
34. Cheng, X. F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236
35. Zhang, L.-S.; Chen, K.; Chen, G.; Li, B.-J.; Luo, S.; Guo, Q.-Y.; Wei, J.-B.; Shi, Z.-J. Org. Lett. 2013, 15, 10
36. Gao, K.; Lee, P.-S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2010, 132, 12249
37. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2010, 49, 6629
38. Gao, K.; Yoshikai, N. J. Am. Chem. Soc. 2011, 133, 400
39. Tsai, A. S.; Tauchert, M. E.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 1248
40. Gao, K.; Yoshikai, N. Angew. Chem., Int. Ed. 2011, 50, 6888
41. Kim, J. Y.; Park, S. H.; Ryu, J.; Cho, S. H.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110
42. Schröder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298
43. Guin, S.; Rout, S. K.; Banerjee, A.; Nandi, A.; Patel, B. K. Org. Lett. 2012, 14, 5294
44. Johnson, D. G.; Lynam, J. M.; Mistry, N. S.; Slattery, J. M.; Thatcher, R. J.; Whitwood, A. C. J. Am. Chem. Soc. 2013, 135, 2222
45. Meng, X.; Kim, S. Org. Lett. 2013, 15, 1910
46. Chan, L. Y.; Kim, S.; Ryu, T.; Lee, P. H. Chem. Commun. 2013, 49, 4682
47. Unoh, Y.; Hashimoto, Y.; Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3258
48. Park, S.; Seo, B.; Shin, S.; Son, J.-Y.; Lee, P. H. Chem. Commun. 2013, 49, 8671
49. Seo, J.; Park, Y.; Jeon, I.; Ryu, T.; Park, S.; Lee, P. H. Org. Lett. 2013, 15, 3358
50. Zhao, D.; Nimphius, C.; Lindale, M.; Glorius, F. Org. Lett. 2013, 15, 4504
51. Chary, B. C.; Kim, S. Org. Biomol. Chem. 2013, 11, 6879
52. Wang, D.-H.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 17676
53. Engle, K. M.; Thuy-Boun, P. S.; Dang, M.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 18183
54. Chan, L. Y.; Cheong, L.; Kim, S. Org. Lett. 2013, 15, 2186
55. For Pd(II)-catalyzed arylation of dialkyl phosphates, see: Jeon, W. H.; Lee, T. S.; Kim, E. J.; Moon, B.; Kang, J. Tetrahedron 2013, 69, 5152
56. Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett. 2011, 13, 1552
57. Petersen, T. B.; Khan, R.; Olofsson, B. Org. Lett. 2011, 13, 3462
58. Kumar, D.; Arun, V.; Pilania, M.; Shekar, K. P. C. Synlett 2013, 831
59. Zhao, J.; Zhang, Y.; Cheng, K. J. Org. Chem. 2008, 73, 7428
60. Yao, J.; Yu, M.; Zhang, Y. Adv. Synth. Catal. 2012, 354, 3205
61. Chu, J.-H.; Lin, P.-S.; Wu, M.-J. Organometallics 2010, 29, 4058
62. Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313
63. Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623
64. Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275
65. Imada, I.; Mitsue, Y.; Washizuka, K.; Murahashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 2079
66. Muzart, J. Tetrahedron 2005, 61, 9423
67. Giannoccaro, P.; Dibenedetto, A.; Gargano, M.; Quaranta, E.; Aresta, M. Organometallics 2008, 27, 967
68. Baker, R.; Sims, R. J. Synthesis 1981, 117
69. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753
70. Zhao, Q.; Sun, J.; Li, J.; He, J. Catal. Commun. 2013, 36, 98
71. Barney, R. J.; Richardson, R. M.; Wiemer, D. F. J. Org. Chem. 2011, 76, 2875