A New Method for the Preparation of Aluminum and Titanium Tris(2,6-diphenylphenoxide) Reagents and Their Application in Organic Synthesis

Chemistry Letters

Volumn 32, Issue 11, 2003, Pages 1006-1007

  Sato, Atsushi ^a   Hattori, Asuka ^a   Ishihara, Kazuaki ^a   Saito, Susumu ^a   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; BENZENE DERIVATIVE; CATION; CHLORINE DERIVATIVE; CHLOROTITANIUM; EPOXIDE; ORGANIC COMPOUND; PINENE; REAGENT; TIN DERIVATIVE; TITANIUM DERIVATIVE; TITANIUM TRIS(2,6 DIPHENYLPHENOXIDE); UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; METHODOLOGY; SYNTHESIS;

EID: 0842328510     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.1006     Document Type: Article

References (21)

1. For review of ATPH, see: a) S. Saito and H. Yamamoto, Chem. Commun., 1997, 2585. Recent application of ATPH, see: b) S. Saito, S. Yamazaki, and H. Yamamoto, Angew. Chem., Int. Ed., 40, 3613 (2001). c) S. Saito, M. Shiozawa, T. Nagahara, M. Nakadai, and H. Yamamoto, J. Am. Chem. Soc., 122, 7847 (2000). d) S. Saito, T. Sone, M. Murase, and H. Yamamoto, J. Am. Chem. Soc., 122, 10216 (2000). e) S. Saito, M. Shiozawa, and H. Yamamoto, Angew. Chem., Int. Ed., 38, 1769 (1999).
2. For review of ATPH, see: a) S. Saito and H. Yamamoto, Chem. Commun., 1997, 2585. Recent application of ATPH, see: b) S. Saito, S. Yamazaki, and H. Yamamoto, Angew. Chem., Int. Ed., 40, 3613 (2001). c) S. Saito, M. Shiozawa, T. Nagahara, M. Nakadai, and H. Yamamoto, J. Am. Chem. Soc., 122, 7847 (2000). d) S. Saito, T. Sone, M. Murase, and H. Yamamoto, J. Am. Chem. Soc., 122, 10216 (2000). e) S. Saito, M. Shiozawa, and H. Yamamoto, Angew. Chem., Int. Ed., 38, 1769 (1999).
3. For review of ATPH, see: a) S. Saito and H. Yamamoto, Chem. Commun., 1997, 2585. Recent application of ATPH, see: b) S. Saito, S. Yamazaki, and H. Yamamoto, Angew. Chem., Int. Ed., 40, 3613 (2001). c) S. Saito, M. Shiozawa, T. Nagahara, M. Nakadai, and H. Yamamoto, J. Am. Chem. Soc., 122, 7847 (2000). d) S. Saito, T. Sone, M. Murase, and H. Yamamoto, J. Am. Chem. Soc., 122, 10216 (2000). e) S. Saito, M. Shiozawa, and H. Yamamoto, Angew. Chem., Int. Ed., 38, 1769 (1999).
4. For review of ATPH, see: a) S. Saito and H. Yamamoto, Chem. Commun., 1997, 2585. Recent application of ATPH, see: b) S. Saito, S. Yamazaki, and H. Yamamoto, Angew. Chem., Int. Ed., 40, 3613 (2001). c) S. Saito, M. Shiozawa, T. Nagahara, M. Nakadai, and H. Yamamoto, J. Am. Chem. Soc., 122, 7847 (2000). d) S. Saito, T. Sone, M. Murase, and H. Yamamoto, J. Am. Chem. Soc., 122, 10216 (2000). e) S. Saito, M. Shiozawa, and H. Yamamoto, Angew. Chem., Int. Ed., 38, 1769 (1999).
5. For review of ATPH, see: a) S. Saito and H. Yamamoto, Chem. Commun., 1997, 2585. Recent application of ATPH, see: b) S. Saito, S. Yamazaki, and H. Yamamoto, Angew. Chem., Int. Ed., 40, 3613 (2001). c) S. Saito, M. Shiozawa, T. Nagahara, M. Nakadai, and H. Yamamoto, J. Am. Chem. Soc., 122, 7847 (2000). d) S. Saito, T. Sone, M. Murase, and H. Yamamoto, J. Am. Chem. Soc., 122, 10216 (2000). e) S. Saito, M. Shiozawa, and H. Yamamoto, Angew. Chem., Int. Ed., 38, 1769 (1999).
6. "Encyclopedia of Reagents for Organic Synthesis," ed. by L. A. Paquette, John Wiley & Sons, Chichester (1995), Vol. 7, p 5186.
7. 4: e) R. W. Chesnut, L. D. Durfee, P. E. Fanwick, and I. P. Rothwell, Polyhedron, 6, 2019 (1987). f) M. G. Thorn, Z. C. Etheridge, P. E. Fanwick, and I. P. Rothwell, J. Organomet. Chem., 591, 148 (1999).
8. 4: e) R. W. Chesnut, L. D. Durfee, P. E. Fanwick, and I. P. Rothwell, Polyhedron, 6, 2019 (1987). f) M. G. Thorn, Z. C. Etheridge, P. E. Fanwick, and I. P. Rothwell, J. Organomet. Chem., 591, 148 (1999).
9. 4: e) R. W. Chesnut, L. D. Durfee, P. E. Fanwick, and I. P. Rothwell, Polyhedron, 6, 2019 (1987). f) M. G. Thorn, Z. C. Etheridge, P. E. Fanwick, and I. P. Rothwell, J. Organomet. Chem., 591, 148 (1999).
10. 4: e) R. W. Chesnut, L. D. Durfee, P. E. Fanwick, and I. P. Rothwell, Polyhedron, 6, 2019 (1987). f) M. G. Thorn, Z. C. Etheridge, P. E. Fanwick, and I. P. Rothwell, J. Organomet. Chem., 591, 148 (1999).
11. 4: e) R. W. Chesnut, L. D. Durfee, P. E. Fanwick, and I. P. Rothwell, Polyhedron, 6, 2019 (1987). f) M. G. Thorn, Z. C. Etheridge, P. E. Fanwick, and I. P. Rothwell, J. Organomet. Chem., 591, 148 (1999).
12. 4: e) R. W. Chesnut, L. D. Durfee, P. E. Fanwick, and I. P. Rothwell, Polyhedron, 6, 2019 (1987). f) M. G. Thorn, Z. C. Etheridge, P. E. Fanwick, and I. P. Rothwell, J. Organomet. Chem., 591, 148 (1999).
13. For the X-ray single crystal structures of various ATPH-carbonyl complexes, see Refs. 1d, 1e and: S. Saito, T. Nagahara, M. Shiozawa, M. Nakadai, and H. Yamamoto, J. Am. Chem. Soc., 125, 6200 (2003).
14. Trioctylmethylsilane (purchased from Shinetsu) was purified by column chromatography and used.
15. 4-n) might be formed.
16. 3ClTi: C, 79.17, H, 4.80%; Found: C, 79.08, H, 4.82%. The single crystals suitable for the X-ray crystal analysis were grown from hexane-benzene at room temperature for 1 to 2 days. A crystal was transferred to a glass capillary tube using a dry-box for the diffraction experiments.
17. w = 0.051, GOF = 1.836, 4989 unique reflections with I > 3.0σ(I). Crystallographic data (excluding structure factors) for the X-ray crystal structure analysis reported in this paper have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication no. CCDC-184707. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambrdge CB2 1EZ, UK (fax: +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk).
18. a) S. Casolari, D. D'Addario, and E. Tagliavini, Org. Lett., 1, 1061 (1999).
19. 2 complex was also reported. See: b) R. O. Duthaler and A. Hafner, Angew. Chem. Int. Ed., 36, 43 (1997). c) D. R. Gauthier, Jr. and E. M. Carreira, Angew. Chem. Int. Ed., 35, 2363 (1996).
20. 2 complex was also reported. See: b) R. O. Duthaler and A. Hafner, Angew. Chem. Int. Ed., 36, 43 (1997). c) D. R. Gauthier, Jr. and E. M. Carreira, Angew. Chem. Int. Ed., 35, 2363 (1996).
21. 2. See: S. Casolari, P. G. Cozzi, P. Orioli, E. Tagliavini, and A. Umani-Ronchi, Chem. Commun., 1997, 2123.