Copper-catalyzed P-arylation via direct coupling of diaryliodonium salts with phosphorus nucleophiles at room temperature

Journal of Organic Chemistry

Volumn 78, Issue 16, 2013, Pages 8176-8183

  Xu, Jian ^a   Zhang, Pengbo ^a   Gao, Yuzhen ^a   Chen, Yiyin ^a   Tang, Guo ^a   Zhao, Yufen ^a,b  

^a XIAMEN UNIVERSITY   (China)

^b Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; DIARYLIODONIUM SALTS; DIRECT COUPLING; ELECTRON-DEFICIENT; LARGE SCALE PREPARATION; NUCLEOPHILIC SUBSTITUTIONS; ROOM TEMPERATURE; SHORT REACTION TIME;

AROMATIC COMPOUNDS; CATALYSIS; CHEMICAL BONDS; NUCLEOPHILES; PHOSPHORUS; SALTS;

COPPER;

COPPER; INORGANIC SALT; NUCLEOPHILE; PHOSPHORUS;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTRON; NUCLEOPHILICITY; REACTION TIME; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; COPPER; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORUS; SALTS; TEMPERATURE;

EID: 84882372966     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4012199     Document Type: Article

References (44)

1. Dang, Q.; Liu, Y.; Cashion, D. K; Kasib-hatla, S. R.; Jiang, T.; Taplin, F.; Jacintho, J. D.; Li, H.; Sun, Z.; Fan, Y.; DaRe, J.; Tian, F.; Li, W.; Gibson, T.; Lemus, R.; van Poelje, P. D.; Potter, S. C.; Erion, M. D. J. Med. Chem. 2011, 54, 153-165
2. Chou, H. H.; Cheng, C. H. Adv. Mater. 2010, 22, 2468-2471
3. Hsu, F. M.; Chien, C. H.; Shu, C. F.; Lai, C. H.; Hsieh, C. C.; Wang, K. W.; Chou, P. T. Adv. Funct. Mater. 2009, 19, 2834-2843
4. McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151-4202
5. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, R. Chem. Rev. 2000, 100, 2741-2769
6. Hirao, T.; Masunaga, T.; Yamada, N. Bull. Chem. Soc. Jpn. 1982, 55, 909-913
7. Zhang, X. H.; Liu, H. Z.; Hu, X. M.; Tang, G.; Zhu, J.; Zhao, Y. F. Org. Lett. 2011, 13, 3478-3481
8. Rmmelt, S. M.; Ranochiari, M.; Bokhoven, J. A. Org. Lett. 2012, 14, 2188-2190
9. Xu, K.; Yang, F.; Zhang, G.; Wu, Y. Green Chem. 2013, 15, 1055-1060
10. Andaloussi, M.; Lindh, J.; Sävmarkar, J.; Sjöberg, P. J. R.; Larhed, M. Chem.-Eur. J. 2009, 15, 13069-13074
11. Zhuang, R. Q; Xu, J.; Cai, Z. S.; Tang, G.; Fang, M. J.; Zhao, Y. F. Org. Lett. 2011, 13, 2110-2113
12. Luo, Y.; Wu, J. Organometallics 2009, 28, 6823-6826
13. Berrino, R.; Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Stabile, P. Org. Biomol. Chem. 2010, 8, 4518-4520
14. Lu, X.; Zhu, J. Synthesis 1987, 726-727
15. Petrakis, K. S.; Nagabhushan, T. L. J. Am. Chem. Soc. 1987, 109, 2831
16. Shen, C.; Yang, G.; Zhang, W. Org. Biomol. Chem. 2012, 10, 3500-3505
17. Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407-409
18. Mu, X. J.; Zou, J. P.; Qian, Q. F.; Zhang, W. Org. Lett. 2006, 8, 5291-5293
19. Hou, C.; Ren, Y.; Lang, R.; Hu, X.; Xia, C.; Li, F. Chem. Commun. 2012, 48, 5181-5183
20. Wen, J.; Zhang, R. Y.; Chen, S. Y.; Zhang, J.; Yu, X. Q. J. Org. Chem. 2012, 77, 766-771
21. Liu, C.; Zhang, W.; Dai, L. X.; You, S. L. Org. Lett. 2012, 14, 4525-4527
22. Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593-1597
23. Kang, S. K.; Lee, H. W.; Jang, S. B.; Kim, T. H.; Pyun, S. J. J. Org. Chem. 1996, 61, 2604-2605
24. Kang, S. K.; Yoon, S. K.; Kim, Y. M. Org. Lett. 2001, 3, 2697-2699
25. Vaddula, B. R.; Saha, A.; Leazer, J.; Varma, R. S. Green Chem. 2012, 14, 2133-2136
26. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052-9070
27. Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett. 2011, 13, 1552-1555
28. Petersen, T. B.; Khan, R.; Olofsson, B. Org. Lett. 2011, 13, 3462-3465
29. Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 188-191
30. Vaddula, B.; Leazer, J.; Varma, R. S. Adv. Synth. Catal. 2012, 354, 986-990
31. Becht, J. M.; Drian, C. L. Org. Lett. 2008, 10, 3161-3164
32. Liu, Z. D.; Chen, Z. C. Synthesis 1993, 373-374
33. Zhou, T.; Chen, Z. C. Synth. Commun. 2001, 31, 3289-3294
34. Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681-684
35. Beringer, F. M.; Falk, R. A.; Karniol, M.; Lillien, I.; Masulio, G.; Mausner, M.; Sommer, E. J. Am. Chem. Soc. 1959, 81, 342-351
36. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299-5358
37. Kitamura, T.; Matsuyuki, J.; Nagata, K.; Furuki, R.; Taniguchi, H. Synthesis 1992, 945-946
38. Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610-2618
39. Kraszkiewicz, L.; Skulski, L. Synthesis 2008, 15, 2373-2380
40. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172-8174
41. Jalalian, N.; Petersen, T. B.; Olofsson, B. Chem.-Eur. J. 2012, 18, 14140-14149
42. Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211-8214
43. Carroll, M. A; Wood, R. A. Tetrahedron 2007, 63, 11349-11354
44. Phipps, R. J; Mcmurray, L.; Ritter, S.; Duong, H. A; Gaunt, M. J J. Am. Chem. Soc. 2012, 134, 10773-10776