Modular synthesis of a new family of tripodal ligands, all-cis-1,2,3- tris(diphenyl-phosphinomethyl)cyclopropane and relatives

Organic Letters

Volumn 9, Issue 14, 2007, Pages 2617-2620

  Schill, Heiko ^a   De Meijere, Armin ^a   Yufit, Dmitry S ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547536644     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070707r     Document Type: Article

References (54)

1. (a) Beller, M.; Zapf, A.; Mägerlein, W. Chem. Eng. Technol. 2001, 24, 575-582.
2. (b) Tucker, C. E.; de Vries, J. G. Top. Catal. 2002, 79, 111-118.
3. (c) Farina, V. Adv. Synth. Catal. 2004, 346, 1553-1582.
4. (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989-1992;
5. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
6. (b) Herrmann, W. A.; Öfele, K. v.; Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229-248.
7. (c) Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055-4082.
8. (d) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2571.
9. (e) de Vries, J. G. Dalton Trans. 2006, 421-429.
10. (a) van Strijdonck, G. P. F.; Boele, M. D. K.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. Eur. J. Inorg. Chem. 1999, 1073-1076.
11. (b) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
12. (c) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. 2004, 116, 1907-1912;
13. Angew. Chem. Int. Ed. 2004, 43, 1871-1876.
14. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
15. (e) Christmann, U.; Vilar, R. Angew. Chem. 2005, 117, 370-378;
16. Angew. Chem. Int. Ed. 2005, 44, 366-374.
17. (a) Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem. 1995, 107, 2602-2605;
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374.
19. (b) Herrmann, W. A.; Òfele, K.; v. Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229-248.
20. (a) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 1633-1637.
21. (b) Feuerstein, M.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 5923-5925.
22. (c) Kondolff, I.; Doucet, H.; Santelli, M. Synlett 2005, 2057-2061.
23. (d) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2005, 46, 1717-1720.
24. (e) Doucet, H.; Santelli, M. Synlett 2006, 2001-2015.
25. For previously prepared cyclopropane-based ligands, see: (a) Aviron-Violet, P.; Colleuille, Y.; Varagnat, J. J. Mol. Catal. 1979, 5, 41-50.
26. (b) Okada, Y.; Minami, T.; Yamamoto, T.; Ichikawa, J. Chem. Lett. 1992, 547-550.
27. (c) Molander, G. A.; Burke, J. P.; Carroll, P. J. J. Org. Chem. 2004, 69, 8062-8069.
28. For studies on the structure of Pd complexes of 1 and a related tetraphosphine ligand, see: (a) Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490-4499. (b) Ref 5e.
29. For a review on bite angles and their importance, see: van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769.
30. (a) D'yakonov, I. A.; Kharicheva, É. M. Zh. Org. Khim. 1966, 2, 372-373;
31. J. Org. Chem. USSR (Engl. Transi.) 1966, 2, 364-365.
32. (b) D'yakonov, I. A.; Kharicheva, É. M. Zh. Org. Khim. 1968, 4, 256-263;
33. J. Org. Chem USSR (Engl. Transl.) 1968, 4, 249-254.
34. (c) Ettlinger, M. G.; Kennedy, F. Chem. Ind. 1957, 891.
35. (d) Ettlinger, M. G.; Kagan, J. Chem. Ind. 1962, 1574.
36. (a) Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441-7444.
37. (b) Gauvry, N.; Huet, F. Tetrahedron 1999, 55, 1321-1328.
38. (c) Gauvry, N.; Comoy, C.; Lescop, C.; Huet, F. Synthesis 1999, 574-576.
39. (a) Mehta, G.; Vidya, R.; Sharma, P. K.; Jemmis, E. D. Tetrahedron Lett. 2000, 41, 2999-3002.
40. (b) Mehta, G.; Gagliardini, V.; Schaefer, C.; Gleiter, R. Org. Lett. 2004, 6, 1617-1620.
41. (a) Charette, A. B.; Gagnon, A.; Fournier, J.-F. J. Am. Chem. Soc. 2002, 124, 386-387.
42. (b) Fournier, J.-F.; Charette, A. B. Eur. J. Org. Chem. 2004, 1401-1404.
43. (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
44. (b) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
45. (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
46. (b) Tsuji, J. In Palladium Reagents and Catalysts -Innovations in Organic Synthesis; Wiley: Chichester, 1995; pp 290-422.
47. (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
48. Sanger, A. R. J. Chem. Soc., Dalton Trans. 1977, 1971-1976. See also refs 5a and 8.
49. 8
50. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. 2001, 113, 2056-2075;
51. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
52. Casey, C. P.; Whiteker, G. T. Isr. J. Chem. 1990, 30, 299-304.
53. As implemented in the Spartan program package: Spartan 04; Wavefunction Inc.: Irvine, CA.
54. Crystallographic data (excluding structure factors) for structure 9 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: (+44)1223-336-033, e-mail: deposit@ccdc.cam.ac.uk], on quoting the depository number CCDC 601835.