Main group redox catalysis: Reversible P III/P V redox cycling at a phosphorus platform

Journal of the American Chemical Society

Volumn 134, Issue 28, 2012, Pages 11330-11333

  Dunn, Nicole L ^a   Ha, Minji ^a   Radosevich, Alexander T ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHENYLHYDRAZINE; MAIN GROUP; PHOSPHORUS SPECIES; REDOX CATALYSIS; REDOX CYCLING; TRANSFER HYDROGENATIONS; TRANSITION METAL CATALYSTS; TWO-ELECTRON REDOX;

CATALYSTS; HYDROGEN; HYDROGENATION; PHOSPHORUS; PHOSPHORUS COMPOUNDS; TRANSITION METALS;

CATALYSIS;

AMMONIA; AZOBENZENE; BORANE DERIVATIVE; PHENYLHYDRAZINE DERIVATIVE; PHOSPHORUS DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL BOND; HYDROGENATION; OXIDATION REDUCTION REACTION; PHOSPHORUS CYCLE;

EID: 84863970203     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja302963p     Document Type: Article

References (45)

1. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley: New York, 1992.
2. Beller, M.; Bolm, C.; Eds. Transition Metals for Organic Synthesis, 2 nd ed.; Wiley: Weinheim, 2004.
3. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross Coupling Reactions; Wiley-VCH: Weinheim, 1998.
4. De Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation; Wiley-VCH, Weinheim, 2007.
5. Ojima, I, Ed. Catalytic Asymmetric Synthesis, 3 rd ed.; Wiley: New York, 2010.
6. Collman, J. P. Acc. Chem. Res. 1968, 1, 136
7. Halpern, J. Acc. Chem. Res. 1970, 3, 386
8. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353
9. Hartwig, J. F. Organotransition Metal Chemistry; University Science Books: Sausalito, CA, 2010; p 261.
10. Martin, D.; Soleilhavoup, M.; Bertrand, G. Chem. Sci. 2011, 2, 389
11. Power, P. P. Nature 2010, 463, 171
12. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46
13. Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202
14. Akiba, K. Y. Chemistry of Hypervalent Compounds; Wiley VCH: New York, 1999.
15. Finet, J.-P. Ligand Coupling Reactions with Heteroatomic Compounds; Elsevier: Oxford; 1998.
16. Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439
17. For C-H activation at a redox active Al(III)-oxo complex, see: Myers, T. W.; Berben, L. A. J. Am. Chem. Soc. 2011, 133, 11865
18. McGonagle, A. E.; Marsden, S. P.; McKever-Abbas, B. Org. Lett. 2008, 10, 2589
19. O'Brien, C. J.; Tellez, J. L.; Nixon, Z. S.; Kang, L. J.; Carter, A. L.; Kunkel, S. R.; Przeworski, K. C.; Chass, G. C. Angew. Chem., Int. Ed. 2009, 48, 6836
20. Cao, J.-J.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2010, 49, 4976
21. Harris, J. R.; Haynes, M. T., II; Thomas, A. M.; Woerpel, K. A. J. Org. Chem. 2010, 75, 5083
22. Denton, R. M.; Jie, A.; Adeniran, B. Chem. Commun. 2010, 46, 3025
23. For a review of organoiodine-catalyzed redox transformations, see: Dohi, T.; Kita, Y. Chem. Commun. 2009, 2073
24. Bullock, R. M. Catalysis without Precious Metals; Wiley VCH: Weinheim, 2010.
25. MacMillan, D. W. C. Nature 2008, 455, 304
26. List, B. Chem. Rev. 2007, 107, 5413
27. Culley, S. A.; Arduengo, A. J. J. Am. Chem. Soc. 1984, 106, 1164
28. Arduengo, A. J.; Stewart, C. A.; Davidson, F.; Dixon, D. A.; Becker, J. Y.; Culley, S. A.; Mizen, M. B. J. Am. Chem. Soc. 1987, 109, 627
29. Arduengo, A. J.; Stewart, C. A. Chem. Rev. 1994, 94, 1215
30. Driess, M.; Muresan, N.; Merz, K.; Pach, M. Angew. Chem., Int. Ed. 2005, 44, 6734
31. Morales-Morales, D.; Jensen, C. M. The Chemistry of Pincer Compounds; Elsevier: Amsterdam, 2007.
32. Choi, J.; MacArthur, A. H. R.; Brookhart, M.; Goldman, A. S. Chem. Rev. 2011, 111, 1761
33. Staubitz, A; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023
34. For a related dihydridophosphorane, see: Murillo, A.; Chiquete, M. L.; Joseph-Nathan, P.; Contreras, R. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 53, 87
35. α-N-Cα′)]. See: Borden, W. T. Chem. Rev. 1989, 89, 1095
36. Gudat, D.; Haghverdi, A.; Nieger, M. Angew. Chem., Int. Ed. 2000, 39, 3084
37. Burck, S.; Gudat, D.; Nieger, M.; Du Mont, W. W. J. Am. Chem. Soc. 2006, 128, 3946
38. Miyake, H.; Kano, N.; Kawashima, T. J. Am. Chem. Soc. 2009, 131, 16622
39. Miyake, H.; Kano, N.; Kawashima, T. Inorg. Chem. 2011, 50, 9083
40. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
41. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
42. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
43. Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535
44. Kenward, A. L.; Piers, W. E. Angew. Chem., Int. Ed. 2007, 47, 38
45. For Lewis base catalysis, see: Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560