Synthesis of annelated phospholes through intramolecular C-H activation by monovalent phosphorus

Angewandte Chemie - International Edition

Volumn 54, Issue 5, 2015, Pages 1583-1586

  Wei, Xinda ^a,b   Lu, Zongming ^a,b   Zhao, Xu ^a,b   Duan, Zheng ^a,b   Mathey, Francois ^a,b  

^a ZHENGZHOU UNIVERSITY   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

Biaryls; C H activation; Insertion; Phosphinidenes; Phospholes

Indexed keywords

ACTIVATION ANALYSIS; PHOSPHORUS;

BIARYLS; C-H ACTIVATION; INSERTION; PHOSPHINIDENES; PHOSPHOLES;

ACTIVATION ENERGY;

EID: 85028168292     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410603     Document Type: Article

References (32)

1. Review: Y. Matano, H. Imahori, Org. Biomol. Chem. 2009, 7, 1258
2. Some recent references: W. Ma, L. Ackerman, Synthesis 2014, 46, 2297
3. B. Wu, M. Santra, N. Yoshikai, Angew. Chem. Int. Ed. 2014, 53, 7543
4. Angew. Chem. 2014, 126, 7673
5. Y. Unoh, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2013, 52, 12975
6. Angew. Chem. 2013, 125, 13213
7. H. Chen, W. Delaunay, J. Li, Z. Wang, P.-A. Bouit, D. Tondelier, B. Geffroy, F. Mathey, Z. Duan, R. Réau, M. Hissler, Org. Lett. 2013, 15, 330
8. K. Baba, M. Tobisu, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11892
9. Angew. Chem. 2013, 125, 12108
10. Y-R. Chen, W.-L. Duan, J. Am. Chem. Soc. 2013, 135, 16754
11. Y. Hayashi, Y. Matano, K. Suda, Y. Kimura, Y. Nakao, H. Imahori, Chem. Eur. J. 2012, 18, 15972
12. Y. Dienes, S. Durben, T. Karpati, T. Neumann, U. Englert, L. Nyulaszi, T. Baumgartner, Chem. Eur. J. 2007, 13, 7487
13. J. G. Cordaro, D. Stein, H. Grützmacher, J. Am. Chem. Soc. 2006, 128, 14962.
14. Recent reviews: J. C. Slootweg, K. Lammertsma, Sci. Synth. 2009, 42, 15
15. R. Waterman, Dalton Trans. 2009, 18
16. M. Rani, Synlett 2008, 2078
17. F. Mathey, Dalton Trans. 2007, 1861
18. K. Lammertsma, Top. Curr. Chem. 2003, 229, 95
19. K. Lammertsma, M. J. M. Vlaar, Eur. J. Org. Chem. 2002, 1127
20. F. Mathey, N. H. Tran Huy, A. Marinetti, Helv. Chim. Acta 2001, 84, 2938.
21. D. H. Champion, A. H. Cowley, Polyhedron 1985, 4, 1791
22. J. Svara, F. Mathey, Organometallics 1986, 5, 1159
23. N. H. Tran Huy, L. Ricard, F. Mathey, New J. Chem. 1998, 22, 75
24. R. E. Bulo, A. W. Ehlers, F. J. J. de Kanter, M. Schakel, M. Lutz, A. L. Spek, K. Lammertsma, B. Wang, Chem. Eur. J. 2004, 10, 2732.
25. A. Marinetti, F. Mathey, J. Fischer, A. Mitschler, J. Chem. Soc. Chem. Commun. 1982, 667.
26. Y. Kuninobu, T. Yoshida, K. Takai, J. Org. Chem. 2011, 76, 7370.
27. F. Mercier, F. Mathey, C. Afiong-Akpan, J.-F. Nixon, J. Organomet. Chem. 1988, 348, 361.
28. Gaussian 03 (Revision B.05), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
29. Review on synthetic aspects: G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11726
30. Angew. Chem. 2013, 125, 11942
31. Theoretical aspects: M. Lein, Coord. Chem. Rev. 2009, 253, 625.
32. CCDC 1012807 (4 f) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.