Phosphinidene complexes of scandium: Powerful PAr Group-transfer vehicles to organic and inorganic substrates

Journal of the American Chemical Society

Volumn 132, Issue 11, 2010, Pages 3691-3693

  Wicker, Benjamin F ^a   Scott, Jennifer ^b   Andino, José G ^a   Gao, Xinfeng ^a   Park, Hyunsoo ^a   Pink, Maren ^a   Mindlola, Daniel J ^a  

^a INDIANA UNIVERSITY   (United States)

^b ROYAL MILITARY COLLEGE OF CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ATE COMPLEX; CHEMICAL EQUATIONS; DFT STUDY; DINUCLEAR; INORGANIC SUBSTRATES; ORGANIC SUBSTRATE; PHOSPHINIDENES; SINGLE CRYSTAL X-RAY DIFFRACTION; TRANSFER VEHICLES;

CHEMICAL REACTIONS; SCANDIUM; SINGLE CRYSTALS; SYNTHETIC FUELS; X RAY DIFFRACTION;

SCANDIUM COMPOUNDS;

ARGON; INORGANIC COMPOUND; ORGANIC COMPOUND; PHOSPHINIC ACID DERIVATIVE; PHOSPHINIDENE COMPLEX; SCANDIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; ION TRANSPORT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 77949840617     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100214e     Document Type: Article

References (55)

1. Giesbrecht, G. R.; Gordon, J. C. Dalton Trans. 2004, 2387.
2. (a) Lammertsma, K.; Vlaar, M. J. M. Eur. J. Org, Chem. 2002, 1127.
3. (b) Cowley, A. H. Acc. Chem. Res. 1997, 30, 445.
4. Cowley, A. H.; Barron, A. R. Acc. Chem. Res. 1988, 21, 81.
5. Mathey, F. Angew. Chem. Int. Ed. 2003, 42, 1578.
6. (e) Shah, S.; Protasiewicz, J. D. Coord. Chem. Rev. 2000, 210, 181.
7. (f) Stephan, D. W. Angew. Chem., Int. Ed. 2000, 39, 314.
8. (g) Lammertsma, K. Top. Curr. Chem. 2003, 229, 95.
9. (h) Mathey, F. Dalton Trans. 2007, 1861.
10. Waterman, R, Dalton Trans. 2009, 18.
11. (j) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy: 1998.From Organophosphorus to Phospha-organic Chemistry; Wiley: NY, 1998.
12. (a) Cummins, C. C.; Schrock, R. R.; Davis, W. M. Angew. Chem. Int. Ed. Engl. 1993, 32, 756.
13. (b) Breen, T. L.; Stephan, D. W. J. Am, Chem. Soc. 117, 11914.
14. (a) Zhao, G.; Basuli, F.; Kilgore, U. J.; Fan, H.; Halikhedkar, A.; Huffman, J. C.; Wu, G.; Mindiola, D. J. J. Am. Chan. Soc. 2006, 128, 13575.
15. (b) Masuda, J. D. ; Hoskin, A. J.; Graham, T. W.; Beddie, C.; Fermin, M. C.; Etkin, N.; Stephan, D. W. Chem-Eur. J. 2006, 12, 8696.
16. (a) Scott, J.; Basuli, F.; Fout, A. R.; Huffman, J. C.; Mindiola, D. J. Aneew. Chem. Int. Ed. 2008, 47, 8502.
17. (b) Scott, J.; Fan, H.; Wicker, B. F.; Fout, A. R.; Baik, M.; Mindiola, D. J. J. Am. Chem. Soc. 2008, 130, 14438.
18. Masuda, J. D.; Jantunen, K. C.; Ozerov, O. V.; Noonan, K. J. T.; Gates, D. P.; Scott, B. L.; Kiplinger, J. L. J. L. J. Am, Chem, Soc. 2008, 130, 2408.
19. See SI.
20. (a) Tsuzuki, S.; Yosida, M.; Uchimaru, T.; Mikami, M. J. Phys. Chem. A 2001, 105, 769.
21. (b) Amunugama, R.; Rodgers, M. T. J. Phys. Chem, A 2002, 106, 5529.
22. Amunugama, R.; Rodgers, M. T. J. Phys. Chem. A 2002, 106, 9092.
23. Amunugama, R.; Rodgers, M. T., Int. J. Mass Svectrom. 2003, 227, 339.
24. (a) Hardman, N. J.; Twamley, B.; Slender, M.; Baldwin, R.; Hino, S.; Schiemenz, B.; Kauzlarich, S. M.; Power, P. P. J. Organomet. Chem. 2002, 643-644, 461.
25. (b) Wehaschulte, R. J.; Power, P. P. J. Am. Chem. Soc. 1997, 119, 2847.
26. Zschunke, A.; Riemer, M.; Schmidt, H.; Issleib, K. Phosnhorus and Sulnhur 1983, 17, 237.
27. Some representative Sc(III)-Br distances (258-28 Â):
28. (a) Neculai, A. M.; Neculai, M.; Nikifarov, G. B.; Roesky, H. W.; Schicker, C.; Herbst-Inner, R.; Magull, J.; Noltemeyer, M. Eur. J. Inorg. Chem. 2003, 3120.
29. (b) Neculai, A. M.; Neculai, M.; Roesky, H. W.; Magull, J.; Baldus, M.; Andronesi, O.; Jansen, M. Oreanometallics 2002, 27, 2590.
30. Ishikawa, S.; Hamada, T.; Manabe, K.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 12236.
31. Hill, N. J.; Levason, W.; Popham, M. C.; Reid, G.; Webster, M., Polyhedron 2002, 25, 1579.
32. (e) Lu, K.; Cui, D. Organometallics 2009, 5438.
33. (a) Neumann, F.; Hampel F.; Schleyer, P. V. R. Inorg. Chem. 1995 34, 6553.
34. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354.
35. A molecular structure of the phosphaalkene is reported m the SI.
36. Umezius, E.; Lam, K.-C.; Rheingold, A. L.; Protasiewicz, J. D. J. Organomet. Chem. 2001, 630, 193.
37. Smith, R. C.; Urnzius, E.; Lan, K.-C.; Rheingold, A. L.; Protasiewicz, J. D. Inorg, Chem. 2002,41, 5296.
38. Shah, S.; Protasiewicz, J. D. Chem. Commun. 1998, 1585.
39. Phospha-Wittig reagents are known to decompose to the diphosphinene and can often form the corresponding primary phosphine, phosphaindole, and/or dihydrophosphanthridine. (a) Umezius, E.; Klippenstein, S. J.; Protasiewicz, J. D. Inorg. Chem. Acta 2000, 297, 181.
40. (b) Shah, S.; Simpson, M. C.; Smith, R. C.; Protasiewicz, J. D. J. Am. Chem Soc. 2001, 123, 6925-6926.
41. Champion, D. H.; Cowley, A. H. Polyhedron 1985, 4, 1791.
42. H-P = 182 Hz):
43. (e) Böhm, V. P. W.; Brookhart, M. Angew. Chem., Int. Ed. 2001, 40, 4694.
44. (f) Stradiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958.
45. Titanium phosphinidenes, although rare, have been reported in the literature, (a) Basuli, F.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc 2003, 125, 10170.
46. (b) Basuli, F.; Watson, L. A.; Huffman, J. C.; Mindiola, D. J. Dalton Trans. 2003, 4228.
47. 1/2 = 100 Hz).
48. (a) Hao, L.; Harrod, J. F. Inorg. Chem. 1999, 2, 191.
49. (b) Kool, L. B.; Rausch, M. D.; Ah, H. G.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew, Chem. Int. Ed. Engl. 1985, 24, 400.
50. 3)Cl were synthesized according to literature procedures and H NMR spectra were compared, with ora mixtures which suggest these species to be likely products formed in the reaction,
51. Pattiasina, J. W.; Heeres, H. J.; Van Bolhuis, F.; Meetsma, A.; Teuben, J. H.; Spek, A. L. Oreanometallics 1987, 6, 2004.
52. (e) Hao, L.; Harrod, J. F. Inorg. Chem. 1999, 2, 191.
53. 3 has been documented. Piro, N. A.; Cummins, C. C. J. Am. Chem, Soc. 2009, 131, 8764.
54. Umezius, E.; Shah, S.; Protasiewicz, J. D. Phosphorus, Sulfur 1999, 137.
55. Kilgore, U. J.; Fan, H.; Pink, M.; Umezius, E.; Protasiewicz, J. D.; Mindiola, D. J, Chem. Common. 2009, 4521.