Intramolecular, Pd/Cu-Co-catalyzed P-C Bond Cleavage and Addition onto an Alkyne: A Route to Benzophospholes

Organic Letters

Volumn 17, Issue 22, 2015, Pages 5722-5724

  Zhou, Yang ^a   Gan, Zhenjie ^a   Su, Bo ^a   Li, Jun ^a   Duan, Zheng ^a   Mathey, François ^a,b  

^a ZHENGZHOU UNIVERSITY   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZENE DERIVATIVE; COPPER; CUPROUS IODIDE; IODIDE; ORGANOPHOSPHORUS COMPOUND; PALLADIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; BENZENE DERIVATIVES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; IODIDES; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PALLADIUM;

EID: 84947996974     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02926     Document Type: Article

References (40)

1. Yeh, W.-Y; Tsai, K.-Y. Organometallics 2010, 29, 604 10.1021/om900914a
2. Kabir, S. E.; Ahmed, F.; Ghosh, S.; Hassan, M. R.; Islam, M. S.; Sharmin, A.; Tocher, D. A.; Haworth, D. T.; Lindeman, S. V.; Siddiquee, T. A.; Bennett, D. W.; Hardcastle, K. I. J. Organomet. Chem. 2008, 693, 2657 10.1016/j.jorganchem.2008.05.001
3. Macgregor, S. A. Chem. Soc. Rev. 2007, 36, 67 10.1039/B516248N
4. Parkins, A. W. Coord. Chem. Rev. 2006, 250, 449 10.1016/j.ccr.2005.08.001
5. Bruce, M. I.; Humphrey, P. A.; Okucu, S.; Schmutzler, R.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2004, 357, 1805 10.1016/j.ica.2004.01.022
6. Gracia, C.; Marco, G.; Navarro, R.; Romero, P.; Soler, T.; Urriolabeitia, E. P. Organometallics 2003, 22, 4910 10.1021/om0305465
7. Keim, W.; Behr, A.; Gruber, B.; Hoffrnann, B.; Kowaldt, F. H.; Kurschner, U.; Limbäcker, B.; Sistig, F. P. Organometallics 1986, 5, 2356 10.1021/om00142a031
8. Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584 10.1021/ic00216a021
9. Garrou, P. E. Chem. Rev. 1985, 85, 171 10.1021/cr00067a001
10. Zhou, H.; Li, J.-X.; Yang, H.-M.; Xia, C.-G.; Jiang, G.-X. Org. Lett. 2015, 17, 4628 10.1021/acs.orglett.5b02366
11. Lu, D.-P.; Xu, Y.; Liu, W.-J.; Guo, L.-J.; Sun, X.-X. Helv. Chim. Acta 2015, 98, 116 10.1002/hlca.201400152
12. Ma, M.-T.; Lu, J.-M. Tetrahedron 2013, 69, 2102 10.1016/j.tet.2013.01.025
13. Li, Z.-Y.; Zhou, H.-P.; Xu, J.-Y.; Wu, X.-M.; Yao, H.-Q. Tetrahedron 2013, 69, 3281 10.1016/j.tet.2013.02.001
14. Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 6166 10.1002/anie.200501582
15. Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. 1998, 37, 481 10.1002/(SICI)1521-3773(19980302)37:4<481::AID-ANIE481>3.0.CO;2-I
16. Kwong, F.-Y.; Lai, C.-W.; Yu, M.; Tian, Y.; Chan, K.-S. Tetrahedron 2003, 59, 10295 10.1016/j.tet.2003.10.061
17. Kwong, F.-Y.; Chan, K.-S. Organometallics 2001, 20, 2570 10.1021/om0100277
18. Kwong, F.-Y.; Chan, K.-S. Organometallics 2000, 19, 2058 10.1021/om9909338
19. Kwong, F.-Y.; Chan, K.-S. Chem. Commun. 2000, 1069 10.1039/b002656p
20. Baba, K.; Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11892 10.1002/anie.201307115
21. Baba, K.; Tobisu, M.; Chatani, N. Org. Lett. 2015, 17, 70 10.1021/ol503252t
22. Cao, J.; Huang, X.; Wu, L.-L. Chem. Commun. 2013, 49, 7747 10.1039/c3cc43640c
23. Xu, Y.-Z.; Wang, Z.-H.; Gan, Z.-J.; Xi, Q.-Z.; Duan, Z.; Mathey, F. Org. Lett. 2015, 17, 1732 10.1021/acs.orglett.5b00598
24. Ren, Y.; Baumgartner, T. Dalton Trans. 2012, 41, 7792 10.1039/c2dt00024e
25. Tsuji, H.; Sato, K.; Sato, Y.; Nakamura, E. Chem.-Asian J. 2010, 5, 1294 10.1002/asia.201000093
26. Tsuji, H.; Sato, K.; Sato, Y.; Nakamura, E. J. Mater. Chem. 2009, 19, 3364 10.1039/b906197e
27. Matano, Y.; Imahori, H. Org. Biomol. Chem. 2009, 7, 1258 10.1039/b819255n
28. Crassous, J.; Réau, R. Dalton Trans. 2008, 6865 10.1039/b810976a
29. Yamaguchi, E.; Wang, C.-G.; Fukazawa, A.; Taki, M.; Sato, Y.; Sasaki, T.; Ueda, M.; Sasaki, N.; Higashiyama, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2015, 54, 4539 10.1002/anie.201500229
30. Gicquel, M.; Zhang, Y.; Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem., Int. Ed. 2015, 54, 5470 10.1002/anie.201500299
31. Wu, B.; Santra, M.; Yoshikai, N. Angew. Chem., Int. Ed. 2014, 53, 7543 10.1002/anie.201404019
32. Ma, S.; Ackermann, L. Synthesis 2014, 46, 2297 10.1055/s-0033-1338630
33. Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 12975 10.1002/anie.201307211
34. Matano, Y.; Hayashi, Y.; Suda, K.; Kimura, Y.; Imahori, H. Org. Lett. 2013, 15, 4458 10.1021/ol401994e
35. Chen, Y.-R.; Duan, W.-L. J. Am. Chem. Soc. 2013, 135, 16754 10.1021/ja407373g
36. Hayashi, Y.; Matano, Y.; Suda, K.; Kimura, Y.; Nakao, Y.; Imahori, H. Chem.-Eur. J. 2012, 18, 15972 10.1002/chem.201203047
37. Fukazawa, A.; Ichihashi, Y.; Kosaka, Y.; Yamaguchi, S. Chem.-Asian J. 2009, 4, 1729 10.1002/asia.200900303
38. Sanji, T.; Shiraishi, K.; Kashiwabara, T.; Tanaka, M. Org. Lett. 2008, 10, 2689 10.1021/ol800841v
39. Tsuji, H.; Sato, K.; Ilies, L.; Itoh, Y.; Sato, Y.; Nakamura, E. Org. Lett. 2008, 10, 2263 10.1021/ol800684x
40. Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230 10.1002/1521-3773(20020902)41:17<3230::AID-ANIE3230>3.0.CO;2-W