P-Arylation of Dialkyl Phosphites and Secondary Phosphine Oxides with Arynes

Journal of Organic Chemistry

Volumn 81, Issue 1, 2016, Pages 276-281

  Chen, Qian ^a   Yan, Xinxing ^a   Du, Zhiyun ^a   Zhang, Kun ^a   Wen, Chunxiao ^a  

^a GUANGDONG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS;

P-ARYLATION; SECONDARY PHOSPHINES; TERTIARY PHOSPHINES;

PHOSPHORUS COMPOUNDS;

ACETONITRILE DERIVATIVE; DEUTERIUM; HYDROGEN; OXIDE; PHOSPHINE DERIVATIVE; PHOSPHITE; TRIPHENYLPHOSPHINE;

ARTICLE; ARYLATION; NUCLEOPHILICITY; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS; TAUTOMERIZATION;

EID: 84953774932     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02308     Document Type: Article

References (57)

1. Kosolapoff, G. M.; Maier, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972.
2. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415 10.1021/cr00044a004
3. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029 10.1021/cr020049i
4. Steininger, H.; Schuster, M.; Kreuer, K. D.; Kaltbeitzel, A.; Bingöl, B.; Meyer, W. H.; Schauff, S.; Brunklaus, G.; Maier, J.; Spiess, H. W. Phys. Chem. Chem. Phys. 2007, 9, 1764 10.1039/b618686f
5. Spampinato, V.; Tuccitto, N.; Quici, S.; Calabrese, V.; Marletta, G.; Torrisi, A.; Licciardello, A. Langmuir 2010, 26, 8400 10.1021/la9048314
6. Shie, J.-J.; Fang, J.-M.; Wang, S.-Y.; Tsai, K.-C.; Cheng, Y.-S. E.; Yang, A.-S.; Hsiao, S.-C.; Su, C.-Y.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11892 10.1021/ja073992i
7. Shie, J.; Fang, J.; Wong, C. Angew. Chem. 2008, 120, 5872 10.1002/ange.200801959
8. Angew. Chem., Int. Ed. 2008, 47, 5788. 10.1002/anie.200801959
9. Wydysh, E. A.; Medghalchi, S. M.; Vadlamudi, A.; Townsend, C. A. J. Med. Chem. 2009, 52, 3317 10.1021/jm900251a
10. Pinault, N. Coord. Chem. Rev. 2003, 241, 1 10.1016/S0010-8545(02)00306-5
11. Knappke, C. E. I.; von Wangelin, A. J. Chem. Soc. Rev. 2011, 40, 4948 10.1039/c1cs15137a
12. Fernández-Pérez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Chem. Rev. 2011, 111, 2119 10.1021/cr100244e
13. Cho, C.-S.; Chen, L.-W.; Chiu, Y.-S. Polym. Bull. 1998, 41, 45 10.1007/s002890050331
14. Cho, C.-S.; Fu, S.-C.; Chen, L.-W.; Wu, T.-R. Polym. Int. 1998, 47, 203 10.1002/(SICI)1097-0126(1998100)47:2<203::AID-PI55>3.0.CO;2-X
15. Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307 10.1351/pac196409020307
16. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415 10.1021/cr00044a004
17. Renard, P.-Y.; Vayron, P.; Leclerc, E.; Valleix, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2003, 42, 2389 10.1002/anie.200250270
18. Jablonkai, E.; Keglevich, G. Curr. Org. Synth. 2014, 11, 429 10.2174/15701794113109990066
19. Jablonkai, E.; Keglevich, G. Org. Prep. Proced. Int. 2014, 46, 281 10.1080/00304948.2014.922376
20. Zhuang, R.; Xu, J.; Cai, Z.; Tang, G.; Fang, M.; Zhao, Y. Org. Lett. 2011, 13, 2110 10.1021/ol200465z
21. Yang, G.; Shen, C.; Zhang, L.; Zhang, W. Tetrahedron Lett. 2011, 52, 5032 10.1016/j.tetlet.2011.07.077
22. Keglevich, G.; Grün, A.; Bölcskei, A.; Drahos, L.; Kraszni, M.; Balogh, G. T. Heteroat. Chem. 2012, 23, 574 10.1002/hc.21053
23. Shen, C.; Yang, G.; Zhang, W. Org. Biomol. Chem. 2012, 10, 3500 10.1039/c2ob25225b
24. Zhang, J.-S.; Chen, T.; Yang, J.; Han, L.-B. Chem. Commun. 2015, 51, 7540 10.1039/C5CC01182E
25. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
26. Börner, A. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Application; Wiley-VCH: Weinheim, 2008.
27. Kamer, P. C. J.; van Leeuwen, P. W. N. M. Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis; Wiley-VCH: Chichester, U.K., 2012.
28. McClure, C. K. Phosphorus in Organic Chemistry; Wiley-VCH: Weinheim, 2012.
29. Li, Y.; Das, S.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727 10.1021/ja301764m
30. Chen, Q.; Zhang, C.; Chen, L.; Wen, C.; Du, Z.; Chen, H.; Zhang, K. Tetrahedron Lett. 2015, 56, 2094 10.1016/j.tetlet.2015.03.005
31. Wen, C.; Chen, Q.; He, Z.; Yan, X.; Zhang, C.; Du, Z.; Zhang, K. Tetrahedron Lett. 2015, 56, 5470 10.1016/j.tetlet.2015.08.019
32. Chen, L.; Zhang, C.; Wen, C.; Zhang, K.; Liu, W.; Chen, Q. Catal. Commun. 2015, 65, 81 10.1016/j.catcom.2015.02.029
33. Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579 10.1002/anie.200600291
34. Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140 10.1039/c2cs15310f
35. Dong, Y.; Liu, B.; Chen, P.; Liu, Q.; Wang, M. Angew. Chem., Int. Ed. 2014, 53, 3442 10.1002/anie.201310340
36. Taniguchi, T.; Curran, D. P. Angew. Chem., Int. Ed. 2014, 53, 13150 10.1002/anie.201408345
37. Hendrick, C. E.; Wang, Q. J. Org. Chem. 2015, 80, 1059 10.1021/jo502541t
38. García-López, J.-A.; Çetin, M.; Greaney, M. F. Org. Lett. 2015, 17, 2649 10.1021/acs.orglett.5b01115
39. Shi, J.; Qiu, D.; Wang, J.; Xu, H.; Li, Y. J. Am. Chem. Soc. 2015, 137, 5670 10.1021/jacs.5b02566
40. Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Lett. 2005, 34, 1538 10.1246/cl.2005.1538
41. Diemer, V.; Berthelot, A.; Bayardon, J.; Jugé, S.; Leroux, F. R.; Colobert, F. J. Org. Chem. 2012, 77, 6117 10.1021/jo3009098
42. Yoshida, S.; Hosoya, T. Chem. Lett. 2013, 42, 583 10.1246/cl.130116
43. Shen, C.; Yang, G.; Zhang, W. Org. Lett. 2013, 15, 5722 10.1021/ol402748u
44. Bhunia, A.; Kaicharla, T.; Porwal, D.; Gonnade, R. G.; Biju, A. T. Chem. Commun. 2014, 50, 11389 10.1039/C4CC05420B
45. Bhunia, A.; Roy, T.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2014, 16, 5132 10.1021/ol502490t
46. Lopez-Leonardo, C.; Raja, R.; López-Ortiz, F.; del águila-Sánchez, M. á.; Alajarin, M. Eur. J. Org. Chem. 2014, 2014, 1084 10.1002/ejoc.201301481
47. Rémond, E.; Tessier, A.; Leroux, F. R.; Bayardon, J.; Jugé, S. Org. Lett. 2010, 12, 1568 10.1021/ol100304c
48. Dhokale, R. A.; Mhaske, S. B. Org. Lett. 2013, 15, 2218 10.1021/ol400780f
49. Bayardon, J.; Laureano, H.; Diemer, V.; Dutartre, M.; Das, U.; Rousselin, Y.; Henry, J.-C.; Colobert, F.; Leroux, F. R.; Jugé, S. J. Org. Chem. 2012, 77, 5759 10.1021/jo300910w
50. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 12, 1211 10.1246/cl.1983.1211
51. Okuma, K.; Nojima, A.; Matsunaga, N.; Shioji, K. Org. Lett. 2009, 11, 169 10.1021/ol802597x
52. Kivrak, A.; Larock, R. C. J. Org. Chem. 2010, 75, 7381 10.1021/jo101656c
53. Rogness, D. C.; Larock, R. C. J. Org. Chem. 2011, 76, 4980 10.1021/jo200651b
54. Deal, E. L.; Petit, C.; Montchamp, J.-L. Org. Lett. 2011, 13, 3270 10.1021/ol201222n
55. Janesko, B. G.; Fisher, H. C.; Bridle, M. J.; Montchamp, J.-L. J. Org. Chem. 2015, 80, 10025 10.1021/acs.joc.5b01618
56. Nitta, Y.; Arakawa, Y. Chem. Pharm. Bull. 1986, 34, 3121 10.1248/cpb.34.3121
57. Kendall, A. J.; Salazar, C. A.; Martino, P. F.; Tyler, D. R. Organometallics 2014, 33, 6171 10.1021/om500854u