Synergic synthesis of benzannulated zincabicyclic complexes, α-Zincated N ylides, through sodium-TM EDA-mediated zincation of a haloarene

Angewandte Chemie - International Edition

Volumn 48, Issue 46, 2009, Pages 8675-8678

  Armstrong, David R ^a   Balloch, Liam ^a   Clegg, William ^b   Dale, Sophie H ^b   García Álvarez, Pablo ^a   Hevia, Eva ^a   Hogg, Loma M ^a   Kennedy, Alan R ^a   Mulvey, Robert E ^a   O'Hara, Charles T ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Alkali metals; Cooperative effects; Metalation; Metallacyclic compounds; Zinc

Indexed keywords

BENZENE RING; COOPERATIVE EFFECTS; METALATION; METALLACYCLIC COMPOUNDS; TETRAMETHYLETHYLENEDIAMINE; ZINCATION;

BENZENE; ZINC;

SODIUM;

EID: 70350599364     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904506     Document Type: Article

References (26)

1. a) S. H. Wunderlich, P. Knöchel, Angew. Chem. 2007,119, 7829;
2. Angew. Chem. Int. Ed. 2007, 46, 7685;
3. b) Z. Dong, G. C. Clososki, S. H. Wunderlich, A. Unsinn, J. Li, P. Knochel, Chem. Eur. J. 2009,15, 457.
4. C. J. Rohbogner, S. H. Wunderlich, G. C. Clososki, P. Knochel, Eur. J. Org. Chem. 2009, 1781.
5. a) Y. Kondo, M. Shilai, M. Uchiyama, T. Sakamoto, J. Am. Chem. Soc. 1999,121, 3539;
6. b) M. Uchiyama, Y. Matsumoto, D. Nobuto, T. Furuyama, K. Yamaguchi, K. Morokuma, J. Am. Chem. Soc. 2006, 128, 8748.
7. P. C. Andrikopoulos, D. R. Armstrong, H. R. L. Barley, W. Clegg, S. H. Dale, E. Hevia, G. W Honeyman, A. R. Kennedy, R. E. Mulvey, J. Am. Chem. Soc. 2005, 127, 6184.
8. R. E. Mulvey, Acc. Chem. Res. 2009, 42, 743.
9. a) T. Harada, M. Chiba, A. Oku, J. Org. Chem. 1999, 64, 8210;
10. b) M. Uchiyama, Y. Kobayashi, T. Furuyama, S. Nakamura, Y. Kajihara, T. Moyashi, T. Sakamoto, Y. Kondo, K. Morokuma, J. Am. Chem. Soc. 2008,130, 472.
11. For reviews of directed ortho-metalation, see: a) H. W Gschwend, H. R. Rodriguez, Org. React. 1979, 26, 1;
12. b) C. G. Hartung, V. Snieckus in Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, New York, 2002, pp. 330-367.
13. For a review of zwitterionic organometalates, see: R. Chauvin, Eur. J. Inorg. Chem. 2000, 577.
14. -3. CCDC 741894 (2), 741895 (3) and 743469 (Int) contain 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.
15. A search of the Cambridge Crystallographic Database revealed no precedent for this structure. There is one example of an azincated phosphorus ylide, see: M. Steiner, H. Grützmacher, H. Pritzkow, L. Zsolnai, Chem. Commun. 1998, 285.
16. W Clegg, B. Conway, E. Hevia, M. D. McCall, L. Russo, R. E. Mulvey, J. Am. Chem. Soc. 2009,131, 2375.
17. M. C. Whisler, S. MacNeil, V. Snieckus, R Beck, Angew. Chem. 2004,116, 2256;
18. Angew. Chem. Int. Ed. 2004, 43, 2206.
19. For examples, see: a) D. Bojer, I. Kamps, X. Tian, A. Hepp, T Pape, R. Fröhlich, N. W. Mitzel, Angew. Chem. 2007,119, 4254;
20. Angew. Chem. Int. Ed. 2007, 46, 4176;
21. b) V. H. Gessner, C. Strohmann, J. Am. Chem. Soc. 2008,130,14412.
22. 3 more acidic, akin to Lewis acid (e.g. borane)-activated amines, see: S. V. Kessar, R Singh, Chem. Rev. 1997, 97, 721.
23. D. V. Graham, E. Hevia, A. R. Kennedy, R. E. Mulvey, Organometallics 2006, 25, 3297.
24. For an enlightening discussion on the role of TMEDA in group 1 chemistry see: D. B. Collum, Acc. Chem. Res. 1992, 25, 448.
25. A. R. Lepley, R. H. Becker, A. G. Giumanini, J. Org. Chem. 1971, 36, 1222.
26. T Morishita, H. Fukushima, H. Yoshida, J. Ohshita, A. Kunai, J. Org. Chem. 2008, 73, 5452, and references therein.