2,5-Dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene: First member of the hetero-DuPHOS family

Journal of Organic Chemistry

Volumn 70, Issue 14, 2005, Pages 5436-5441

  Benincori, Tiziana ^a   Pilati, Tullio ^b   Rizzo, Simona ^b   Sannicolò, Franco ^b,c,d   Burk, Mark J ^e   De Ferra, Lorenzo ^f   Ullucci, Elio ^f   Piccolo, Oreste ^g  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

^d Dipartimento di Chimica Organica e Industriale   (Italy)

^e DIVERSA CORPORATION   (United States)

^f Chemi SpA   (Italy)

^g Studio di Consulenza Scientifica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL BONDS; HYDROGENATION; RATE CONSTANTS; SYNTHESIS (CHEMICAL);

CARBON-OXYGEN DOUBLE BONDS; ENANTIOMERIC ACCESS (EA); LIGANDS; THIOPHENE;

AROMATIC COMPOUNDS;

1,2 BIS(PHOSPHOLANO)BENZENE; 2,5 DIMETHYL 3,4 BIS(2,5 DIMETHYLPHOSPHOLANO)THIOPHENE; CARBON; RHODIUM COMPLEX; RUTHENIUM COMPLEX; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 22144457089     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050390d     Document Type: Article

References (22)

1. (a) Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E. J. Chem. Soc. Chem. Commun. 1995, 685-686.
2. (b) Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244-.
3. (c) Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T.; Zotti, G. J. Organomet. Chem. 1997, 529, 445-453.
4. (d) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolò, F. J. Org. Chem. 2000, 65, 2043-2047.
5. (e) Benincori, T.; Rizzo, S.; Sannicolò, F. J. Heterocycl. Chem. 2002, 39, 471-485.
6. Benincori, T.; Piccolo, O.; Rizzo, S.; Sannicolò, F. J. Org. Chem. 2000, 65, 8340-8347.
7. Celentano, G.; Benincori, T.; Radaelli, S.; Sada, M.; Sannicolò, F. J. Organomet. Chem. 2002, 643-644, 424-430.
8. (a) Tietze, L. F.; Thede, K. J. Chem. Soc. Chem. Commun. 1999, 1811-1812:
9. (b) Tietze, L. F.; Thede, K.; Sannicolò, F.; Schimpf, R. J. Chem. Soc. Chem. Commun. 2000, 583-584.
10. Tietze, L. F.; Lohmann, J. K. Synlett 2002, 2083-2085.
11. Burk, J. M.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
12. Sannicolò, F.; Piccolo, O.; Benincori, T.; Sada, M.; Verrazzani, A.; Tollis, S.; Ullucci, E.; De Ferra, L.; Rizzo, S. Patent WO03074169; Patent EP1490173.
13. Some ligands displaying two homomorphic phospholane units bound to the 2,3-positions of electron-poor thianaphthene have been prepared by a past co-worker of one of us and patented by Solvias. These diphosphines are asymmetric, since the two phospholane rings are located on constitutionally heterotopic carbon atoms.
14. 2 symmetric bis(phospholane) ligands characterized by nonaromatic, very electron poor maleic anhydride and maleinimide as scaffolds for the phospholane rings. Patent WO03084971.
15. 1d currently produced at a kiloscale level at Chemi S.p.A.
16. Diphosphinobenzene can be also prepared on a scale through a photochemical reaction between dichlorobenzene and trimethyl phosphite, followed by reduction with LAH/TMSCl (see: Kyba et al. Organometallics 1983, 2, 1877-1879).
17. p = 0.65 V).
18. Fors, K. S.; Gage, J. R. J. Org. Chem. 1998, 63, 7348-7356.
19. Burk, M. J.; Harper, T. G. P., Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423-4424.
20. Herseczki, Z.; Gergely, I.; Hegedüs, C.; Szöllösy, Bakos, J. Tetrahedron: Asymmetry 2004, 15, 1673-1676.
21. Repetitive venting of the autoclave for sampling sometimes produces degradation of the catalyst with consequent rate depression.
22. Sheldrick, G. M. SHELXL-97. Program for the Refinement of Crystal Structures; University of Göttingen, Germany.