Enantiofacial discrimination in dihapto-coordination of aromatic molecules by the chiral π-base/σ-Lewis acid {TpRe(CO)(PME3)} [2]

Journal of the American Chemical Society

Volumn 121, Issue 27, 1999, Pages 6499-6500

  Brent Gunnoe, T ^a   Sabat, Michal ^a   Dean Harman, W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND;

CHIRALITY; COMPLEX FORMATION; ENANTIOMER; LETTER; MOLECULAR INTERACTION;

EID: 0345552052     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990891e     Document Type: Letter

References (30)

1. See, for example: (a) Semmelhack, M. F. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, p 489. (b) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994, Chapter 10.
2. See, for example: (a) Semmelhack, M. F. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, p 489. (b) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994, Chapter 10.
3. Harman, W. D. Chem. Rev. 1997, 97, 1953.
4. 2+, see: (a) Barrera, J.; Orth, S. D.; Harman, W. D. J. Am. Chem. Soc. 1992, 114, 7316. (b) Orth, S. D.; Barrera, J.; Rowe, S. M.; Helberg, L. E.; Harman, W. D. lnorg. Chim. Acta 1998, 270.337. In addition, the dicationic nature limits solvent environments and purification techniques.
5. 2+, see: (a) Barrera, J.; Orth, S. D.; Harman, W. D. J. Am. Chem. Soc. 1992, 114, 7316. (b) Orth, S. D.; Barrera, J.; Rowe, S. M.; Helberg, L. E.; Harman, W. D. lnorg. Chim. Acta 1998, 270.337. In addition, the dicationic nature limits solvent environments and purification techniques.
6. 2-aromatic complexes are rare. For examples of dihapto-bound aromatic complexes, see ref 6.
7. Helberg, L. E.; Orth, S. D.; Sabat, M.; Harman, W. D. Inorg. Chem. 1996, 35, 5584; Brooks, B. C.; Chin, R. M.; Harman, W. D. Organometallics 1998, 77, 4716.
8. Helberg, L. E.; Orth, S. D.; Sabat, M.; Harman, W. D. Inorg. Chem. 1996, 35, 5584; Brooks, B. C.; Chin, R. M.; Harman, W. D. Organometallics 1998, 77, 4716.
9. Gunnoe, T. B.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1998, 120, 8747.
10. For recent reviews of hydridotris(pyrazolyl)borate liganda, see: (a) Kitajima, N.; Tolman, W. D. Prog, Inorg. Chem. 1995, 43, 419. (b) Trofimenko, S. Chem. Rev. 1993, 93, 943. (c) Trofimenko, S. Prog. Inorg. Chem. 1986, 34, 115.
11. For recent reviews of hydridotris(pyrazolyl)borate liganda, see: (a) Kitajima, N.; Tolman, W. D. Prog, Inorg. Chem. 1995, 43, 419. (b) Trofimenko, S. Chem. Rev. 1993, 93, 943. (c) Trofimenko, S. Prog. Inorg. Chem. 1986, 34, 115.
12. For recent reviews of hydridotris(pyrazolyl)borate liganda, see: (a) Kitajima, N.; Tolman, W. D. Prog, Inorg. Chem. 1995, 43, 419. (b) Trofimenko, S. Chem. Rev. 1993, 93, 943. (c) Trofimenko, S. Prog. Inorg. Chem. 1986, 34, 115.
13. 2(O) was first reported in Abrams, M. J.; Davison, A.; Jones, A. G. Inorg. Chim. Acta 1984, 82, 125.
14. (b) Mayer and Brown have reported an improved synthesis: Brown, S. N.; Mayer, J. M. Inorg. Chem. 1992, 31, 4091.
15. 2(pyridine) reported by Mayer and Brown: Brown, S. N.; Mayer, J. M. Organometallics 1995, 14, 2951.
16. 3 complexes. For example, see: Cusanelli, A.; Sutton, D. Organometallics 1995, 14, 4651.
17. Back-bonding of the two dπ Orbitals which are oriented along the Re-CO bond axis with the strongly π-acidic CO ligands will result in substantial lowering of the energy of these two Orbitals.
18. For reports of structural features of similar rhenium-alkene complexes, see: (a) Kowalczyk, J. J.; Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729. (b) Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686.
19. For reports of structural features of similar rhenium-alkene complexes, see: (a) Kowalczyk, J. J.; Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729. (b) Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686.
20. The majority of the protons of complex 4 were located in the Fourier map. However, due possibly to disorder, H(3) and H(17) were not located in the Fourier map, and these hydrogens were placed at calculated positions.
21. [ReTp(CO)(L)(naphthalene)] complexes (where L = pyridine and tert-butylisonitrile) have also been prepared recently in our laboratories. These systems show two resolved diastereomers at 20°C.
22. (a) Gladysz, J. A.; Boone, B. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 550.
23. (b) See p 557 of ref 14(a).
24. For fall details of these studies, see the Supporting Information.
25. (a) Angelici, R. I. Coord. Chem. Rev. 1990, 105, 61.
26. (b) Choi, M.-G.; Angelici, R. J. J. Am. Chem. Soc. 1990, 112, 7811 and references therein.
27. (a) Harris, S. Organometalics 1994, 13, 2628.
28. (b) Palmer, M. S.; Rowe, S.; Harris, S. Organometallics 1998, 17, 3798.
29. (a) Winemiller, M. D.; Harman, W. D. J. Am. Chem. Soc. 1998, 120, 7835.
30. (b) See Supporting Information for details.